Editing Elias James Corey

{{Short description|American chemist (born 1928)}}
{{Infobox scientist
| name              = E.J. Corey
| image             = E.J.Coreyx240.jpg
| image_size        = 240px
| caption           = Corey in 2007
| birth_name        = Elias James Corey
| birth_date        = {{Birth date and age|1928|07|12|mf=yes}}
| birth_place       = [[Methuen, Massachusetts]], U.S.
| alma_mater        = [[Massachusetts Institute of Technology]] ([[B. S.|BS]], [[PhD]])
| doctoral_advisor  = [[John C. Sheehan]]
| thesis_title      = The synthesis of N,N-diacylamino acids and analogs of penicillin
| thesis_year       = 1951
| thesis_url        = http://www.worldcat.org/oclc/30308926
| notable_students  = {{Plainlist|
* [[Phil Baran]]
* [[Rajender Leleti]]
* [[Eric Block]]
* [[Dale L. Boger]]
* [[Weston T. Borden]]
* [[David E. Cane]]
* [[Rick L. Danheiser]]
* [[William L. Jorgensen]]
* [[John Katzenellenbogen]]
* [[Alan P. Kozikowski]]
* [[Bruce H. Lipshutz]]
* [[David R. Liu|David Liu]]
* [[Gojko Lalic]]
* [[Albert Meyers]]
* [[K. C. Nicolaou]]
* [[Ryōji Noyori]]
* [[Gary H. Posner]]
* [[Bengt I. Samuelsson]]
* [[Dieter Seebach]]
* [[Vinod K. Singh]]
* [[Brian Stoltz]]
* [[Hisashi Yamamoto]]
* [[Ramakanth Sarabu]]
* [[Jin-Quan Yu]]
}}
| known_for = {{Plainlist|
* [[Retrosynthetic analysis]]
* [[Synthon]]
* [[CBS catalyst|Corey–Bakshi–Shibata catalyst]]
* [[Johnson–Corey–Chaykovsky reaction|Corey–Chaykovsky reaction]]
* [[Corey–Fuchs reaction]]
* [[Corey–Gilman–Ganem oxidation]]
* [[Corey–House synthesis]]
* [[Corey–Itsuno reduction]]
* [[Corey–Kim oxidation]]
* [[Corey–Link reaction]]
* [[Corey–Nicolaou macrolactonization]]
* [[Peterson olefination#Variations|Corey–Peterson olefination]]
* [[Corey–Seebach reaction]]
* [[Pyridinium chlorochromate|Corey–Suggs reagent]]
* [[Corey–Winter olefin synthesis]]
* [[LHASA]]
}}
| website           = {{URL|http://chemistry.harvard.edu/people/e-j-corey}}
| field             = [[Organic chemistry]]
| work_institutions = [[University of Illinois at Urbana–Champaign]]<br/>[[Harvard University]]
| prizes            = {{Plainlist|
* [[ACS Award in Pure Chemistry]]  (1960)
* [[Ernest Guenther Award]] (1968)
* [[Centenary Medal]] (1971)
* [[Linus Pauling Award]] (1973)
* [[George Ledlie Prize]] (1973)
* [[Arthur C. Cope Award]] (1976)
* [[William H. Nichols Medal]] (1977)
* [[Franklin Medal]] (1978)
* [[Chemical Pioneer Award]] (1981)
* [[Lewis S. Rosenstiel Award]] (1981)
* [[Paul Karrer Gold Medal]] (1982)
*  [[Tetrahedron Prize]] (1983)
* [[Willard Gibbs Award]] (1984)
* [[Wolf Prize in Chemistry]] (1986)
* [[National Medal of Science]] (1988)
* [[Japan Prize]] (1989)<ref name=jp>[http://www.japanprize.jp/en/laureates_by_year1980.html Laureates of the Japan Prize] {{webarchive |url=https://web.archive.org/web/20160407130947/http://www.japanprize.jp/en/laureates_by_year1980.html |date=April 7, 2016 }}. japanprize.jp</ref>
* [[Nobel Prize in Chemistry]] (1990)
* [[Fellow of the Royal Society|ForMemRS]] (1998)<ref name=formemrs/>
* [[Priestley Medal]] (2004)}}
}}
'''Elias James Corey''' (born July 12, 1928) is an American [[organic chemistry|organic chemist]]. In 1990, he won the [[Nobel Prize in Chemistry]] "for his development of the theory and methodology of [[organic synthesis]]",<ref>{{cite web | title = The Nobel Prize in Chemistry 1990 | publisher = Nobelprize.org | url = http://nobelprize.org/nobel_prizes/chemistry/laureates/1990/index.html|access-date=July 25, 2015}}</ref> specifically [[retrosynthetic analysis]].<ref>E. J. Corey, X-M. Cheng, ''The Logic of Chemical Synthesis'', Wiley, New York, 1995, {{ISBN|0-471-11594-0}}.</ref><ref name=nobel-lecture>{{cite journal | last1 = Corey | first1 = E.J. | year = 1991 | title = The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture) | journal = [[Angew. Chem. Int. Ed. Engl.]] | volume = 30 | issue = 5| pages = 455–465 | doi = 10.1002/anie.199104553 }}</ref>  

Regarded by many as one of the greatest living chemists, he has developed numerous synthetic [[reagents]], methodologies and total syntheses and has advanced the science of organic synthesis considerably.

==Biography==
E.J. Corey (the surname was anglicized from [[Levantine Arabic]] ''[[Khoury]]'', meaning ''priest'') was born to [[Lebanese Greek Orthodox Christians|Lebanese Greek Orthodox Christian]] immigrants Fatima (née Hasham) and Elias Corey in [[Methuen, Massachusetts]], {{convert|50|km|mi|abbr=on}} north of Boston.<ref>[http://nobelprize.org/chemistry/laureates/1990/corey-autobio.html Elias James Corey – Autobiography] {{webarchive |url=https://web.archive.org/web/20080706111206/http://nobelprize.org/chemistry/laureates/1990/corey-autobio.html |date=July 6, 2008 }}. nobelprize.org</ref> His mother changed his name from William to "Elias" to honor his father, who died eighteen months after Corey's birth. His widowed mother, brother, two sisters, aunt and uncle all lived together in a spacious house, struggling through the [[Great Depression]]. As a young boy, Corey was independent and enjoyed sports such as baseball, football, and hiking. He attended a Catholic elementary school and [[Lawrence High School (Massachusetts)|Lawrence High School]] in [[Lawrence, Massachusetts]].

At the age of 16 Corey entered [[MIT]], where he earned both a [[bachelor's degree]] in 1948 and a [[Doctor of Philosophy|Ph.D.]] under Professor [[John C. Sheehan]] in 1951. Upon entering MIT, Corey's only experience with science was in mathematics, and he began his college career pursuing a degree in engineering. After his first chemistry class in his sophomore year he began rethinking his long-term career plans and graduated with a bachelor's degree in chemistry. Immediately thereafter, at the invitation of Professor John C. Sheehan, Corey remained at MIT for his Ph.D. After his graduate career he was offered an appointment at the [[University of Illinois at Urbana–Champaign]], where he became a full professor of chemistry in 1956 at the age of 27. He was initiated as a member of the Zeta chapter of [[Alpha Chi Sigma]] at the University of Illinois in 1952.<ref name="alphachisigma.org">[http://www.alphachisigma.org/page.aspx?pid=268 Fraternity – Awards – Hall of Fame – Alpha Chi Sigma<!-- Bot generated title -->] {{webarchive |url=https://web.archive.org/web/20160126172333/http://www.alphachisigma.org/page.aspx?pid=268 |date=January 26, 2016 }}</ref> In 1959, he moved to [[Harvard University]], where he is currently an emeritus professor of organic chemistry with an active Corey Group research program. He chose to work in organic chemistry because of "its intrinsic beauty and its great relevance to human health".<ref>{{cite news
  | last = Corey
  | first = E.J.
  | title = Nobel Prize Autobiography
  | publisher = Nobelprize.org: The Official Site of the Nobel Prize
  | year = 1990
  | url = http://nobelprize.org/nobel_prizes/chemistry/laureates/1990/corey.html
  | access-date = September 9, 2010}}
</ref> He has also been an advisor to Pfizer for more than 50 years.<ref>{{cite news
  | title = Compiled Works of Elias J. Corey, Notes, Pfizer, Celebrating your 80th birthday
  | date = June 27, 2008
  | url = http://ejcorey.org/corey/notes/notes.php
  | access-date = November 15, 2013}}
</ref>

Among numerous honors, Corey was awarded the [[National Medal of Science]] in 1988,<ref>[https://www.nsf.gov/od/nms/recip_details.cfm?recip_id=88 National Science Foundation – The President's National Medal of Science] {{webarchive |url=https://web.archive.org/web/20121015222720/https://www.nsf.gov/od/nms/recip_details.cfm?recip_id=88 |date=October 15, 2012 }}</ref> the [[Nobel Prize in Chemistry]] in 1990,<ref name=nobel-lecture/> and the [[American Chemical Society]]'s greatest honor, the [[Priestley Medal]], in 2004.<ref name=major-awards/>

==Major contributions==

===Reagents===
Corey has developed several new synthetic reagents: <ul>
<li>[[pyridinium chlorochromate|PCC (pyridinium chlorochromate)]], also referred to as the '''Corey-Suggs reagent''', is widely used for the oxidation of [[Alcohol (chemistry)|alcohol]]s to corresponding [[ketone]]s and [[aldehyde]]s.<ref name=PCC />  PCC has several advantages over other commercial oxidants.  An air-stable yellow solid, it is only slightly hygroscopic. Unlike other oxidizing agents, PCC requires only about 1.5 equivalents <!--as opposed to excess?--> to complete a single oxidation (scheme 1). 
[[File:PCC mechanism.png|700px|center]]
In the reaction, the alcohol nucleophilically displaces chlorine from the electropositive [[chromium]](VI) metal. The [[chloride]] [[anion]] then acts as a base to afford the aldehyde product and chromium(IV).

The slightly acidic character of PCC makes it useful for cyclization reactions with alcohols and [[alkene]]s (Scheme 2).<ref name="acidic chromium oxidation" />
[[File:PCC under acidic conditions2.png|700px|center|reactivity of PCC under acidic conditions]]
The initial oxidation yields the corresponding aldehyde, which can then undergo a [[Prins reaction]] with the neighboring [[alkene]]. After elimination and further oxidation, the product is a cyclic [[ketone]]. Conversely, powdered [[sodium acetate]] co-reagent inhibits reaction after formation of the aldehyde.

PCC's oxidatory robustness has also rendered it useful in the realm of total synthesis (Scheme 3). This example illustrates that PCC is capable of performing a ''Dauben oxidative rearrangement'' with tertiary alcohols through a [3,3]-sigmatropic rearrangement.<ref name=Dauben />
[[File:PCC rearrangement3.png|700px|center|[3,3] rearrangement with PCC]]
</li>
<li>''t''-Butyldimethylsilyl ether (TBS),<ref name=TBS /> triisopropylsilyl ether (TIPS), and methoxyethoxymethyl (MEM) are popular alcohol [[protecting group]]s. The development of these protecting groups allowed the synthesis of several [[natural product]]s whose [[functional group]]s could not withstand standard chemical transformations. Although the synthetic community attempts to minimize the use of protecting groups, it is still rare that a published natural-product synthesis omits them entirely.

Since 1972 the TBS group has become the most popular [[silicon]] protecting group (Scheme 4).<ref name=TBSPop1 /><ref name=TBSPop2 />  TBS is stable to [[chromatography]] and labile enough to cleave under basic and acidic conditions. More importantly, TBS [[ether]]s are stable to such carbon nucleophiles as Grignard reagents and enolates.<ref>Kocienski, P.J. ''Protecting Groups''; Georg Thieme Verlag: Germany, 2000</ref><ref>{{cite journal | last1 = Friesen | first1 = R. W. | display-authors = etal   | year = 1991 | title = A highly stereoselective conversion of α-allenic alcohols to 1,2-syn amino alcohol derivatives via iodocarbamation | journal = Tetrahedron Lett. | volume = 31 | issue = 30| pages = 4249–4252 | doi = 10.1016/S0040-4039(00)97592-0 }}</ref><ref>{{cite journal | last1 = Imanieh | display-authors = etal   | year = 1992 | title   =A facile generation of α-silyl carbanions| journal = Tetrahedron Lett. | volume = 33 | issue = 4| pages = 543–546 | doi=10.1016/s0040-4039(00)93991-1}}</ref>
[[File:TBS primary deprotection4.png|500px|center]]

[[Camphorsulfonic acid|CSA (Camphorsulfonic acid)]] selectively removes a primary TBS ether in the presence of TIPS and tertiary TBS ethers. Other TBS deprotection methods include acids (also Lewis acids), and [[fluoride]]s.

TIPS protecting groups provide increased selectivity of primary over secondary and tertiary alcohol protection. Their ethers are more stable under acidic and basic conditions than TBS ethers, but less labile for deprotection.<ref>{{cite journal | last1 = Ogilvie | display-authors = etal   | year = 1974 | title   =Selective protection of hydroxyl groups in deoxynucleosides using alkylsilyl reagents.| journal = Tetrahedron Lett. | volume = 116 | issue = 33| pages = 2865–2868 | doi = 10.1016/s0040-4039(01)91764-2 }}</ref> The most common cleavage reagents employ the same conditions as TBS ether, but longer reaction times.
[[File:Primary TIPS deprotection5.png|550px|center]]
Usually TBAF severs TBS ethers, but the hindered TBS ether above survives primary TIPS removal (scheme 5).<ref>{{cite journal | last1 = Kadota | display-authors = etal   | year = 1998 | title   =Stereocontrolled Total Synthesis of Hemibrevetoxin B| journal = J. Org. Chem. | volume = 63 | issue = 19| pages = 6597–6606 | doi=10.1021/jo9807619}}</ref>

The MEM protecting group was first described by Corey in 1976.<ref>{{cite journal | last1 = Corey | display-authors = etal   | year = 1976 | title   =A new general method for protection of the hydroxyl function| journal = Tetrahedron Lett. | volume = 17 | issue = 11| pages = 809–812 | doi=10.1016/s0040-4039(00)92890-9}}</ref> This protecting group is similar in reactivity and stability to other alkoxy methyl ethers under acidic conditions. Acidic conditions usually accomplish cleavage of MEM protecting groups, but coordination with metal halides greatly enhances lability  (scheme 6).<ref>{{cite journal | last1 = Chiang | display-authors = etal   | year = 1989 | title   =Total synthesis of L-659,699, a novel inhibitor of cholesterol biosynthesis| journal = J. Org. Chem. | volume = 54 | issue = 24| pages = 5708–5712 | doi=10.1021/jo00285a017}}</ref> 
[[File:MEM Zn deprotection6.png|600px|center]]</li>
<li>1,3-[[Dithiane]]s are a temporary modification of a [[carbonyl]] group that reverses their reactivity in displacement and addition reactions. Dithianation introduced ''[[umpolung]]'' chemistry, now a key concept in organic synthesis.<ref name=Dithianes />

The formations of dithianes can be accomplished with a Lewis acid (scheme 7) or directly from carbonyl compounds.<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Seebach | first2 = D. | year = 1965 | title   =Synthesis of 1,n-Dicarbonyl Derivates Using Carbanions from 1,3-Dithianes| journal = Angew. Chem. Int. Ed. | volume = 4 | issue = 12| pages = 1077–1078 | doi=10.1002/anie.196510771}}</ref>
[[File:Dithiane formation7.png|350px|center]]
The pKa of dithianes is approximately 30, allowing deprotonation with an alkyl lithium reagent, typically [[n-butyllithium]].

The reaction between dithianes and aldehydes is now known as the [[Corey-Seebach reaction]]. The dithiane, once deprotonated, serves as an acyl anion, attacking incoming [[electrophile]]s. Dithiane deprotection, usually with HgO, constructs a ketone product.<ref name=Dithianes>{{cite journal | last1 = Corey | display-authors = etal   | year = 1982 | title   =Total synthesis of aplasmomycin| journal = Journal of the American Chemical Society | volume = 104 | issue = 24| pages = 6818–6820 | doi = 10.1021/ja00388a074 | bibcode = 1982JAChS.104.6818C }}</ref> 
[[File:1,2-dithiane addition8.png|650px|center]]</li>
<li>Corey also commenced detailed studies on cationic polyolefin cyclizations utilized in enzymatic production of [[cholesterol]] from simpler plant terpenes.<ref>{{cite journal | last1 = Wendt | first1 = K.U. | last2 = Schulz | first2 = G.E. | last3 = Liu | first3 = D.R. | last4 = Corey | first4 = E.J. | year = 2000 | title   =Enzyme Mechanisms for Polycyclic Triterpene Formation| journal = [[Angewandte Chemie International Edition in English]] | volume = 39 | issue = 16| pages = 2812–2833 | doi = 10.1002/1521-3773(20000818)39:16<2812::aid-anie2812>3.3.co;2-r | pmid = 11027983 }}</ref> Corey established the details of the remarkable cyclization process by first studying the biological synthesis of sterols from squalene.</li>
</ul>

===Methodology===
Several reactions developed in Corey's lab have become commonplace in modern synthetic organic chemistry.  At least 302 methods have been developed in the Corey group since 1950.<ref>See the Methods tab{{cite news
  | title = Compiled Works of Elias J. Corey
  | date = July 12, 2008
  | url = http://ejcorey.org/corey/methods/methods.php
  | access-date = November 15, 2013}}
</ref> Several reactions have been named after him: <ul>
<li>[[Corey-Itsuno reduction]], also known as the Corey-Bakshi-Shibata reduction, is an enantioselective reduction of ketones to alcohols through an oxazaborolidine [[Catalysis|catalyst]], with various boranes as the stoichiometric reductant.<ref>{{cite journal | last1 = Corey | first1 = E. J. | display-authors = etal   | year = 1998 | title   =Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method| journal = Angew. Chem. Int. Ed. | volume = 37 | issue = 15| pages = 1986–2012 | doi = 10.1002/(sici)1521-3773(19980817)37:15<1986::aid-anie1986>3.0.co;2-z | pmid = 29711061 }}</ref>

The Corey group first demonstrated [[CBS catalyst|the catalyst's]] synthesis using borane and the chiral amino acid [[proline]] (scheme 9).<ref name=reactions>Kürti, L.; Czakó, B. ''Strategic Applications of Named Reactions in Organic Synthesis''; Elsevier: Burlington, 2005.</ref><ref name=enantioselective>Corey, E.J.; Kürti, L. ''Enantioselective Chemical Synthesis''; Direct Book Publishing: Dallas, 2010</ref>
[[File:CBS formation9.png|center|600px]]
Later, Corey demonstrated that substituted boranes were easier to prepare and much more stable.

The reduction mechanism begins with the oxazoborolidine, only slightly basic at [[nitrogen]], coordinating to a borane reductant (scheme 10).<ref name="enantioselective"/> Poor donation from the nitrogen to the boron leaves the Lewis acidity mostly intact, allowing coordination to the ketone substrate. The complexation of the substrate occurs from the most accessible lone pair of the [[oxygen]], restricting rotation around the B-O bond due to the sterically neighboring phenyl group.<ref>{{cite journal | last1 = Corey | first1 = E.J. | last2 = Bakshi | first2 = R.K. | last3 = Shibata | first3 = S. | year = 1987 | title   =Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications| journal = Journal of the American Chemical Society | volume = 109 | issue = 18| pages = 5551–5553 | doi = 10.1021/ja00252a056 | bibcode = 1987JAChS.109.5551C }}</ref>
[[File:CBS mechanism10.png|center|400px]]
Migration of the hydride from borane to the electrophilic ketone center occurs via a 6-membered ring transition state, leading to a four-membered ring intermediate, ultimately providing the chiral product and regeneration of the catalyst.<ref name=ReferenceA />

The reaction has also been of great use to natural products chemists (scheme 11).<ref name="ReferenceA">{{cite journal | last1 = Corey | display-authors = etal   | year = 1987 | title   =A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses| journal = Journal of the American Chemical Society | volume = 109 | issue = 25| pages = 7925–7926 | doi = 10.1021/ja00259a075 | bibcode = 1987JAChS.109.7925C }}</ref><ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Roberts | first2 = B. E. | year = 1997 | title   =Total Synthesis of Dysidiolide| journal = Journal of the American Chemical Society | volume = 119 | issue = 51| pages = 12425–12431 | doi = 10.1021/ja973023v | bibcode = 1997JAChS.11912425C }}</ref> The synthesis of dysidiolide by Corey and co-workers was achieved via an enantioselective CBS reduction using a borane-dimethylsulfide complex. 
[[File:CBS total synthesis11.png|550px|center]]</li>
<li>[[Corey-Fuchs reaction|Corey-Fuchs alkyne synthesis]] is the synthesis of terminal [[alkyne]]s through a one-carbon homologation of aldehydes using [[triphenylphosphine]] and carbon tetrabromide.<ref name="reactions"/><ref>Corey, E.J.; Fuch, P.L. ''Tetrahedron Lett.'' '''1972''', 3769</ref> The mechanism is similar to that of a combined [[Wittig reaction]] and [[Appell reaction]]. Reacting a phosphorus ylide formed ''in situ'' with the aldehyde substrate yields a dibromoolefin.<ref>Eymery ''et al'' ''Synthesis'' '''2000''', 185</ref>
[[File:Corey-fuch reaction12.png|550px|center]]
On treatment with two equivalents of ''n''-butyllithium, lithium halogen exchange and deprotonation yields a lithium acetylide species that undergoes hydrolysis to yield the terminal alkyne product (scheme 12).<ref name="reactions"/>

More recent developments include a modified procedure for one-pot synthesis.<ref>{{cite journal | last1 = Michel | display-authors = etal   | year = 1999 | title   =A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes| journal = Tetrahedron Lett. | volume = 40 | issue = 49| pages = 8575–8578 | doi=10.1016/s0040-4039(99)01830-4}}</ref>

This synthetic transformation has been proven successful in the total synthesis (+)-taylorione by W.J. Kerr and co-workers (scheme 13).<ref>{{cite journal | last1 = Donkervoot | display-authors = etal   | year = 1996 | title   =Development of modified Pauson-Khand reactions with ethylene and utilisation in the total synthesis of (+)-taylorione| journal = Tetrahedron | volume = 52 | issue = 21| pages = 7391–7420 | doi = 10.1016/0040-4020(96)00259-1 }}</ref>
[[File:Corey-fuch total synthesis13.png|550px|center]]</li>
<li>The [[Corey–Kim oxidation]] was a new conversion of alcohols into corresponding aldehydes and ketones.<ref name="reactions"/><ref name="CoreyKim">{{cite journal | last1 = Corey | first1 = E.J. | last2 = Kim | first2 = C. U. | year = 1972 | title   =New and highly effective method for the oxidation of primary and secondary alcohols to carbonyl compounds| journal = [[Journal of the American Chemical Society]] | volume = 94 | issue = 21| pages = 7586–7587 | doi = 10.1021/ja00776a056 | bibcode = 1972JAChS..94.7586C }}</ref><ref>{{cite journal | title = A method for the oxidation of sec,tert-1,2-diols to α-hydroxy ketones without carbon-carbon cleavage |author1=E. J. Corey |author2=C. U. Kim | journal =  [[Tetrahedron Letters]]| year = 1974| volume = 15| issue = 3| pages = 287–290| doi =  10.1016/S0040-4039(01)82195-X}}</ref> This combination of ''N''-chlorosuccinimidosulfonium chloride (NCS), dimethylsulfide (DMS), and [[triethylamine]] (TEA) offers a less toxic alternative to chromium-based oxidations.

The Corey-Kim reagent is formed in ''situ'' when the succinimide and sulfide react to form a dimethylsuccinimidosulfonium chloride species (scheme 14).<ref name="reactions"/>
[[File:Corey kim ox14.png|550px|center]]
Triethylamine deprotonates the alkoxysulfonium salt at the α position to afford the oxidized product. The reaction accommodates a wide array of functional groups, but allylic and benzylic alcohols are typically transformed into chlorides instead.<ref name="CoreyKim"/>

Its application in synthesis is based on the mild protocol conditions and functional and protecting group compatibility. In the total synthesis of ingenol, Kuwajima and co-workers exploited the Corey-Kim oxidation by selectively oxidizing the less hindered secondary alcohol(scheme 15).<ref>{{cite journal | last1 = Kuwajima | display-authors = etal   | year = 2003 | title   =Total Synthesis of Ingenol| journal = Journal of the American Chemical Society | volume = 125 | issue = 6| pages = 1498–1500 | doi = 10.1021/ja029226n | pmid = 12568608   | bibcode = 2003JAChS.125.1498T }}</ref>
[[File:Corey kim ox synthesis example15.png|550px|center]]</li>
<li>[[Corey-Winter Olefination|Corey-Winter olefination]] is a stereospecific transformation of 1,2-diols to alkenes involving the diol substrate, thiocarbonyldiimidazole, and excess trialkylphosphite.<ref name="reactions"/><ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Winter | first2 = A. E. | year = 1963 | title   =A New, Stereospecific Olefin Synthesis from 1,2-Diols| journal = Journal of the American Chemical Society | volume = 85 | issue = 17| pages = 2677–2678 | doi = 10.1021/ja00900a043 | bibcode = 1963JAChS..85.2677C }}</ref>

The exact mechanism is unknown, but has been narrowed down to two possible pathways.<ref>{{cite book |last1=Block |title=Organic Reactions |year=1984 |isbn=978-0-471-26418-7 |volume=30 |page=457 |chapter=Olefin Synthesis by Deoxygenation of Vicinal Diols |doi=10.1002/0471264180.or030.02 |display-authors=}}</ref> The thionocarbonate and trialkylphosphite either form a phosphorus ylide or carbenoid intermediate.

The reaction is stereospecific for most substrates unless the product would lead to an exceedingly strained structure, as discovered when Corey ''et al'' attempted to form sterically hindered ''trans'' alkenes in certain 7-membered rings.

Stereospecfic alkenes are present in several natural products as the method continues to be exploited to yield a series of complex substrates. Professor T.K.M Shing ''et al'' used the Corey-Winter olefination reaction to synthesize (+)-Boesenoxide (scheme 16).<ref>{{cite journal | last1 = Shing | display-authors = etal   | year = 1998 | title   =Enantiospecific Syntheses of (+)-Crotepoxide, (+)-Boesenoxide, (+)-β-Senepoxide, (+)-Pipoxide Acetate, (−)- iso -Crotepoxide, (−)-Senepoxide, and (−)-Tingtanoxide from (−)-Quinic Acid 1| journal = J. Org. Chem. | volume = 63 | issue = 5| pages = 1547–1554 | doi = 10.1021/jo970907o }}</ref>
[[File:Corey-winter olefination example16.png|600px|center|total synthesis example of corey winter olefination]]</li>
<li>CBS-type enantioselective [[Diels–Alder reaction]] has been developed using a similar scaffold to the enantioselective CBS reduction.<ref name="enantioselective"/> After the development of this reaction the CBS reagent proved to be a very versatile reagent for a series of several powerful synthetic transformations. The use of a chiral Lewis acid such as the CBS catalyst includes a broad range of unsaturated [[enone]]s substrates.

The reaction likely proceeds via a highly organized 6-membered ring pre-transition state to deliver highly enantio-enriched products (scheme 17).<ref>{{cite journal | last1 = Nair | display-authors = etal   | year = 2007 | title   =Intramolecular 1,3-dipolar cycloaddition reactions in targeted syntheses| journal = Tetrahedron | volume = 63 | issue = 50| pages = 12247–12275 | doi=10.1016/j.tet.2007.09.065}}</ref> 
[[File:Diels alder TS17.png|400px|center|enantioslective diels-alder transition state]]
This transition state likely occurs because of favorable pi-stacking with the phenyl substituent.<ref name="enantioselective"/><ref>{{cite journal | last1 = Corey | first1 = E. J. | display-authors = etal   | year = 2004 | title   =Enantioselective and Structure-Selective Diels−Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules| journal = J. Am. Chem. Soc. | volume = 126 | issue = 15| pages = 4800–4802 | doi = 10.1021/ja049323b | pmid = 15080683 | bibcode = 2004JAChS.126.4800R }}</ref> The enantioselectivity of the process is facilitated from the diene approaching the dienophile from the opposite face of the phenyl substituent.

The Diels-Alder reaction is one of the most powerful transformations in synthetic chemistry. The synthesis of natural products using the Diels-Alder reaction as a transform has been applied especially to the formation of six-membered rings(scheme 18).<ref>{{cite journal | last1 = Corey | display-authors = etal   | year = 1994 | title   =Demonstration of the Synthetic Power of Oxazaborolidine-Catalyzed Enantioselective Diels-Alder Reactions by Very Efficient Routes to Cassiol and Gibberellic Acid| journal = J. Am. Chem. Soc. | volume = 116 | issue = 8| pages = 3611–3612 | doi=10.1021/ja00087a062| bibcode = 1994JAChS.116.3611C }}</ref>
[[File:Diels alder example enantioselective18.png|600px|center|enantioslective diels-alder in total synthesis]]</li>
<li>[[Corey-Nicolaou macrolactonization]] provides the first method for preparing medium-to-large-size [[lactone]]s.<ref name="reactions"/><ref>{{cite journal | last1 = Corey | display-authors = etal   | year = 1975 | title   =Synthesis of novel macrocyclic lactones in the prostaglandin and polyether antibiotic series| journal = Journal of the American Chemical Society | volume = 97 | issue = 3| pages = 653–654 | doi = 10.1021/ja00836a036 | pmid = 1133366 | bibcode = 1975JAChS..97..653C }}</ref> Previously, intermolecular outcompeted intramolecular lactonization even at low concentrations. One big advantage of this reaction is that it is performed under neutral conditions allowing the presence of acid and base-labile functional groups. As of 2016, rings of 7–44 members have been successfully synthesized using this method.<ref>{{cite journal | last1 = Nicolaou | first1 = K. C. | year = 1977 | title   =Synthesis of macrolides| journal = Tetrahedron | volume = 33 | issue = 7| pages = 683–710 | doi=10.1016/0040-4020(77)80180-4}}</ref><ref>{{Cite journal |last1=Shin |first1=Inji |last2=Hong |first2=Suckchang |last3=Krische |first3=Michael J. |date=2016-11-02 |title=Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C–C Bond Formation |journal=Journal of the American Chemical Society |language=en |volume=138 |issue=43 |pages=14246–14249 |doi=10.1021/jacs.6b10645 |issn=0002-7863 |pmc=5096380 |pmid=27779393|bibcode=2016JAChS.13814246S }}</ref> 
[[File:Corey-nicolaou macrolactonization19.png|600px|center|mechanism of Corey-Nicolaou macrolactonization]]

The reaction occurs in the presence of 2,2'-dipyridyl disulfide and triphenylphosphine with reflux of a nonpolar solvent such as [[benzene]]. The mechanism begins with formation of the 2-pyridinethiol ester (scheme 19). Proton-transfer provides a dipolar intermediate in which the alkoxide [[nucleophile]] attacks the electrophilic carbonyl center, providing a tetrahedral intermediate that yields the macrolactone product.<ref name=Macrolactones />

One of the first examples of this protocol was applied to the total synthesis of [[zearalenone]] (scheme 20).<ref name=Macrolactones>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Nicolaou | first2 = K. C. | year = 1974 | title   =Efficient and mild lactonization method for the synthesis of macrolides| journal = Journal of the American Chemical Society | volume = 96 | issue = 17| pages = 5614–5616 | doi = 10.1021/ja00824a073 | bibcode = 1974JAChS..96.5614C }}</ref>
[[File:Macrolactonization example20.png|600px|center|macrolactonization total synthesis example]]</li>
<li>The [[Johnson-Corey-Chaykovsky reaction]] synthesizes [[epoxide]]s and [[cyclopropane]]s.<ref name="reactions"/> The reaction forms a sulfur ylide in situ that reacts with enones, ketones, aldehydes, and [[imine]]s to form corresponding epoxides, cyclopropanes, and [[aziridines]].<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Chaykovsky | year = 1962 | title   =Dimethylsulfoxonium Methylide| journal = Journal of the American Chemical Society | volume = 84 | issue = 5| pages = 867–868 | doi = 10.1021/ja00864a040 | bibcode = 1962JAChS..84..867C }}</ref> Two sulfur ylide variants have been employed that give different chemeoselective products (scheme 21).The dimethylsulfoxonium methylide provides epoxides from ketones, but yields the cyclopropanes when enones are employed. Dimethylsulfonium methylide transforms ketones and enones to the corresponding epoxides. Dimethylsulfonium methylide is much more reactive and less stable than dimethylsulfoxonium methylide, so it is generated at low temperatures.<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Chaykovsky | year = 1965 | title   =Dimethyloxosulfonium Methylide ((CH<sub>3</sub>)<sub>2</sub>SOCH<sub>2</sub>) and Dimethylsulfonium Methylide ((CH<sub>3</sub>)<sub>2</sub>SCH<sub>2</sub>). Formation and Application to Organic Synthesis|journal = Journal of the American Chemical Society | volume = 87 | issue = 6| pages = 1353–1364 | doi = 10.1021/ja01084a034 | bibcode = 1965JAChS..87.1353C }}</ref> 
[[File:Corey-chakovsky reaction21.png|600px|center|corey-chaykovsky selectivity]]</li>

<li>Based on their reactivity, another distinct advantage of these two variants is that kinetically they provide a difference in diastereoselectivity. The reaction is very well established, and enantioselective variants (catalytic and stoichiometric) have also been achieved. From a retrosynthetic analysis standpoint, this reaction provides a reasonable alternative to conventional epoxidation reactions with alkenes (scheme 22). Danishefsky utilized this methodology for the synthesis of taxol. Diastereoselectivity is established by 1,3 interactions in the transition state required for epoxide closure.<ref>{{cite journal | last1 = Danishefsky | display-authors = etal   | year = 1996 | title   =Total Synthesis of Baccatin III and Taxol| journal = Journal of the American Chemical Society | volume = 118 | issue = 12| pages = 2843–2859 | doi = 10.1021/ja952692a | bibcode = 1996JAChS.118.2843D }}</ref>
[[File:Corey-chakovsky example22.png|600px|center|corey-chaykovsky total synthesis example]]</li>
</ul>

===Total syntheses===
E. J. Corey and his research group have completed many [[total synthesis|total syntheses]]. At least 265 natural compounds have been synthesized in the Corey group since 1950.<ref>See the Syntheses tab{{cite news
  | title = Compiled Works of Elias J. Corey
  | publisher = ejcorey.org
  | date = July 12, 2008
  | url = http://ejcorey.org/corey/syntheses/syntheses.php
  | access-date = November 15, 2013}}
</ref>

His 1969 total syntheses of several [[prostaglandin]]s are considered classics.<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Weinshenker | first2 = N. M. | last3 = Schaaf | first3 = T. K. | last4 = Huber | first4 = W. | year = 1969 | title   =Stereo-controlled synthesis of dl-prostaglandins F2.alpha. and E2| journal = [[J. Am. Chem. Soc.]] | volume = 91 | issue = 20| pages = 5675–5677 | doi = 10.1021/ja01048a062 | pmid=5808505| bibcode = 1969JAChS..91.5675C }}</ref><ref>[[K. C. Nicolaou]], E. J. Sorensen, ''Classics in Total Synthesis'', VCH, New York, 1996, {{ISBN|3-527-29231-4}}.</ref><ref>{{cite journal|author1=Corey, E. J. |author2=Schaaf, T. K. |author3=Huber, W. |author4=Koelliker,V. |author5=Weinshenker, N. M. |title=Total Synthesis of Prostaglandins F<sub>2α</sub> and E<sub>2</sub> as the Naturally Occurring Forms|journal=Journal of the American Chemical Society|volume=92|issue=2|pages=397–8|doi=10.1021/ja00705a609|pmid=5411057|year=1970}}</ref><ref>For a review see Axen, U.; Pike, J. E.; and Schneider, W. P. (1973) p. 81 in ''The Total Synthesis of Natural Products'', Vol. 1, ApSimon, J. W. (ed.) Wiley, New York.</ref> Specifically the synthesis of Prostaglandin F<sub>2α</sub> presents several challenges. The presence of both ''cis'' and ''trans'' olefins as well as five asymmetric carbon atoms renders the molecule a desirable challenge for organic chemists. Corey's retrosynthetic analysis outlines a few key disconnections that lead to simplified precursors (scheme 23). 
[[File:Prostaglandin retro23.png|600px|center]]
Molecular simplification began first by disconnecting both carbon chains with a Wittig reaction and Horner-Wadsworth Emmons modification. The Wittig reaction affords the ''cis'' product, while the Horner-Wadsworth Emmons produces the ''trans'' olefin. The published synthesis reveals a 1:1 diastereomeric mixture of the carbonyl reduction using zinc borohydride. However, years later Corey and co-workers established the CBS reduction. One of the examples that exemplified this protocol was an intermediate in the prostaglandin synthesis revealing a 9:1 mixture of the desired diastereomer (scheme 24).<ref name="ReferenceA"/> 
[[File:Prostoglandin CBS24.png|500px|center]]
The iodolactonization transform affords an allylic alcohol leading to a key Baeyer-Villiger intermediate. This oxidation regioselectively inserts an oxygen atom between the ketone and the most electron-rich site. The pivotal intermediate leads to a straightforward conversion to the Diels-Alder structural goal, which provides the carbon framework for the functionalized cyclopentane ring. Later Corey developed an asymmetric Diels-Alder reaction employing a chiral oxazoborolidine, greatly simplifying the synthetic route to the prostaglandins.

Other notable syntheses: 
* [[Longifolene]]<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Ohno | first2 = M. | last3 = Vatakencherry | first3 = P. A. | last4 = Mitra | first4 = R. B. | year = 1961 | title   =TOTAL SYNTHESIS OF d,l-LONGIFOLENE| journal = [[J. Am. Chem. Soc.]] | volume = 83 | issue = 5| pages = 1251–1253 | doi = 10.1021/ja01466a056 | bibcode = 1961JAChS..83.1251C }}</ref><ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Ohno | first2 = M. | last3 = Mitra | first3 = R. B. | last4 = Vatakencherry | first4 = P. A. | year = 1964 | title = Total Synthesis of Longifolene | journal = [[J. Am. Chem. Soc.]] | volume = 86 | issue = 3| pages = 478–485 | doi = 10.1021/ja01057a039 | bibcode = 1964JAChS..86..478C }}</ref>
* [[Ginkgolide]]s A<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Ghosh | first2 = A. K. | year = 1988 | title   =Total synthesis of ginkgolide a| journal = [[Tetrahedron Lett.]] | volume = 29 | issue = 26| pages = 3205–3206 | doi=10.1016/0040-4039(88)85122-0| pmc = 6781876 | pmid = 31595095 }}</ref> and B<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Kang | first2 = M. | last3 = Desai | first3 = M. C. | last4 = Ghosh | first4 = A. K. | last5 = Houpis | first5 = I. N. | year = 1988 | title   =Total synthesis of (.+-.)-ginkgolide B| journal = [[J. Am. Chem. Soc.]] | volume = 110 | issue = 2| pages = 649–651 | doi=10.1021/ja00210a083| pmid = 31527923 | pmc = 6746322 | bibcode = 1988JAChS.110..649C }}</ref><ref>{{cite journal | last1 = Corey | first1 = E. J. | year = 1988 | title   =Robert Robinson Lecture. Retrosynthetic thinking?essentials and examples| journal = [[Chem. Soc. Rev.]] | volume = 17 | pages = 111–133 | doi=10.1039/cs9881700111}}</ref>
* [[Lactacystin]]<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Reichard | first2 = G. A. | year = 1992 | title = Total Synthesis of Lactacystin | journal = [[J. Am. Chem. Soc.]] | volume = 114 | issue = 26| pages = 10677–10678 | doi=10.1021/ja00052a096| bibcode = 1992JAChS.11410677C }}</ref>
* [[Miroestrol]]<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Wu | first2 = L. I. | year = 1993 | title = Enantioselective Total Synthesis of Miroestrol | journal = [[J. Am. Chem. Soc.]] | volume = 115 | issue = 20| pages = 9327–9328 | doi=10.1021/ja00073a074| bibcode = 1993JAChS.115.9327C }}</ref>
* [[Ecteinascidin 743]]<ref>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Gin | first2 = D. Y. | last3 = Kania | first3 = R. S. | year = 1996 | title   =Enantioselective Total Synthesis of Ecteinascidin 743| journal = [[J. Am. Chem. Soc.]] | volume = 118 | issue = 38| pages = 9202–9203 | doi=10.1021/ja962480t| bibcode = 1996JAChS.118.9202C }}</ref>
* [[Salinosporamide A]]<ref>{{cite journal | last1 = Reddy Leleti | first1 = Rajender | last2 = Corey | first2 = E. J. | year = 2004 | title = A Simple Stereocontrolled Synthesis of Salinosporamide A| journal = [[J. Am. Chem. Soc.]] | volume = 126| issue = 20| pages = 6230–6232 | doi = 10.1021/ja048613p | pmid = 15149210| bibcode = 2004JAChS.126.6230R | citeseerx = 10.1.1.472.2554 }}</ref>

===Computer programs===
Corey and his research group created [[LHASA]], a program that uses [[artificial intelligence]] to discover sequences of reaction which may lead to total synthesis.<ref>{{Cite journal |last1=Corey |first1=E. J. |last2=Wipke |first2=W. Todd |last3=Cramer |first3=Richard D. |last4=Howe |first4=W. Jeffrey |date=1972-01-01 |title=Computer-assisted synthetic analysis. Facile man-machine communication of chemical structure by interactive computer graphics |url=https://pubs.acs.org/doi/abs/10.1021/ja00757a020 |journal=Journal of the American Chemical Society |language=en |volume=94 |issue=2 |pages=421–430 |doi=10.1021/ja00757a020 |bibcode=1972JAChS..94..421C |issn=0002-7863}}</ref> The program was one of the first to use a graphical interface to input and display chemical structures.<ref>{{Cite journal |last1=Wang |first1=Zhuang |last2=Zhang |first2=Wenhan |last3=Liu |first3=Bo |date=2021-06-26 |title=Computational Analysis of Synthetic Planning: Past and Future |url=https://onlinelibrary.wiley.com/doi/10.1002/cjoc.202100273 |journal=Chinese Journal of Chemistry |language=en |volume=39 |issue=11 |pages=3127–3143 |doi=10.1002/cjoc.202100273 |issn=1001-604X}}</ref>

===Publications===
E.J. Corey has more than 1100 publications.<ref>See Publications in {{cite news
  | title = Compiled Works of Elias J. Corey
  | publisher = ejcorey.org
  | date = November 15, 2013
  | url = http://ejcorey.org/corey/index.html
  | access-date = November 15, 2013}}
</ref> In 2002, the American Chemical Society (ACS) recognized him as the "Most Cited Author in Chemistry".  In 2007, he received the first ACS Publications Division "Cycle of Excellence High Impact Contributor Award"<ref>{{cite news
  | last = Baum
  | first = Rudy
  | title = E.J. Corey: Chemist Extraordinaire
  | publisher = C&EN Meeting Weblog, 234th ACS National Meeting &Exposition, August 19–23, 2007, Boston, Massachusetts.
  | date = August 21, 2007
  | url = http://cenboston.wordpress.com/2007/08/21/ej-corey-chemist-extraordinaire/
  | access-date = September 8, 2010}}
</ref> and was ranked the number one chemist in terms of research impact by the Hirsch Index ([[h-index]]).<ref>{{cite news
  | last = Van Noorden
  | first = Richard
  | title = Hirsch index ranks top chemists
  | publisher = RSC: Advancing the Chemical Sciences, Chemistry World
  | date = April 23, 2007
  | url = http://www.rsc.org/chemistryworld/News/2007/April/23040701.asp
  | access-date = September 9, 2010}}
</ref> His books include:
* {{cite book | last=Corey | first=E. J. | title=Enantioselective chemical synthesis : methods, logic and practice | publisher=Direct Book Publishing | publication-place=Dallas, Texas | year=2010 | isbn=978-0-615-39515-9 | oclc=868975499 | page=}}
* {{cite book | last=Corey | first=E. J. | title=The logic of chemical synthesis | publisher=John Wiley | publication-place=New York | year=1995 | isbn=0-471-11594-0 | oclc=45734016 | page=}}
* {{cite book | last=Corey | first=E. J. | title=Molecules and medicine | publisher=John Wiley & Sons | publication-place=Hoboken, N.J | year=2007 | isbn=978-0-470-26096-8 | oclc=156819246 | page=}}
* {{cite book | last=Li | first=Jie | title=Name Reactions in Heterocyclic Chemistry II | publisher=Wiley | publication-place=Hoboken, N.J | year=2011 | isbn=978-0-470-08508-0 | oclc=761319808 | page=}}
* {{cite book | last=Li | first=Jie | title=Name reactions for functional group transformations | publisher=Wiley-Interscience | publication-place=Hoboken, N.J | year=2007 | isbn=978-0-471-74868-7 | oclc=85851580 | page=}}

==Altom suicide==
{{Main|Jason Altom}}
[[Jason Altom]], one of Corey's students, committed suicide in 1998.<ref name=chronicle_suicide>{{cite news |last=Schneider |first=Alison |title=Harvard Faces the Aftermath of a Graduate Student's Suicide |work=The Chronicle of Higher Education |year=1998 |url=http://chronicle.com/article/Harvard-Faces-the-Aftermath-of/6469/ |access-date=August 21, 2010 }}</ref>  Altom's suicide caused controversy because he explicitly blamed Corey, his research advisor, for his suicide.<ref name= NYTAltom>{{cite news
  | last = Hall
  | first = Stephen S.
  | title = Lethal Chemistry at Harvard
  | work=The New York Times
  | date = November 29, 1998
  | url = https://query.nytimes.com/gst/fullpage.html?res=9D00E5DB1F30F93AA15752C1A96E958260
  }}
</ref> Altom cited in his 1998 farewell note "abusive research supervisors" as one reason for taking his life. Altom's suicide note also contained explicit instructions on how to reform the relationship between students and their supervisors.

Altom was the third member of Corey's lab to commit suicide since 1980.<ref>{{cite news |last1=Hall |first1=Stephen |title=Lethal Chemistry at Harvard |url=https://www.nytimes.com/1998/11/29/magazine/lethal-chemistry-at-harvard.html |access-date=September 26, 2020 |work=New York Times |date=December 29, 1998}}</ref> Corey was reportedly devastated and bewildered by his student's death.<ref name=Globe>English, Bella. {{cite web |url=http://www.boston.com/dailyglobe2/002/living/Grad_student_suicides_spur_big_charges_at_Harvard_chem_labs+.shtml |title=Grad-student suicides spur big changes at Harvard chem labs |access-date=November 24, 2010 |url-status=bot: unknown |archive-url=https://web.archive.org/web/20010124052200/http://www.boston.com/dailyglobe2/002/living/Grad_student_suicides_spur_big_charges_at_Harvard_chem_labs+.shtml |archive-date=January 24, 2001 }}, ''[[The Boston Globe]]'' via Archive.org (January 2, 2001).</ref> Corey said, "That letter doesn't make sense. At the end, Jason must have been delusional or irrational in the extreme." Corey also claimed he never questioned Altom's intellectual contributions. "I did my best to guide Jason as a mountain guide would to guide someone climbing a mountain. I did my best every step of the way," Corey states. "My conscience is clear. Everything Jason did came out of our partnership. We never had the slightest disagreement."<ref name=chronicle_suicide /> The [[American Foundation for Suicide Prevention]] (AFSP) cited ''[[The New York Times]]'' article on Altom's suicide as an example of problematic reporting, arguing that Altom presented warning signs of depression and suicidal ideation and that the article had scapegoated Corey despite a lack of secondary evidence that the advisor's behavior had contributed to Altom's distress.<ref>{{cite news
  | title = For the Media: Examples of Good and Problematic Reporting, Scapegoating, New York Times Magazine: Lethal Chemistry at Harvard
  | publisher = American Foundation for Suicide Prevention (AFSP)
  | year = 2010
  | url = https://www.afsp.org/index.cfm?fuseaction=home.viewpage&page_id=92569BDA-A491-50C6-17ED3B1618AF3291
  | archive-url = https://web.archive.org/web/20060925213645/http://www.afsp.org/index.cfm?fuseaction=home.viewpage&page_id=92569BDA-A491-50C6-17ED3B1618AF3291
  | url-status = dead
  | archive-date = September 25, 2006
  | access-date = November 4, 2012}}
</ref><ref>The AFSP incorrectly identifies the author and date of ''The New York Times'' article as Keith B. Richburg and November 28, 1998.  The author was Stephen S. Hall and the date of publication was November 29, 1998.{{cite news
  | last = H
  | first = H
  | author2=M.A.
  | title = For the Media: Problematic Reporting, Scapegoating
  | publisher = American Foundation for Suicide Prevention (AFSP)
  | year = 2010
  | url = https://www.afsp.org/index.cfm?fuseaction=home.viewpage&page_id=92569BDA-A491-50C6-17ED3B1618AF3291
  | archive-url = https://web.archive.org/web/20060925213645/http://www.afsp.org/index.cfm?fuseaction=home.viewpage&page_id=92569BDA-A491-50C6-17ED3B1618AF3291
  | url-status = dead
  | archive-date = September 25, 2006
  | access-date = August 21, 2010}}
</ref> According to ''[[The Boston Globe]]'', students and professors said Altom actually retained Corey's support.<ref name=Globe />
==Corey Group members==
As of 2010, approximately 700 people have been Corey Group members including notable students [[Eric Block]],
[[Dale L. Boger]], [[Weston T. Borden]], [[David E. Cane]], [[Rick L. Danheiser]], [[William L. Jorgensen]], [[John Katzenellenbogen]], [[Alan P. Kozikowski]], [[Bruce H. Lipshutz]], [[David R. Liu]], [[Albert Meyers]], [[K. C. Nicolaou]], [[Ryōji Noyori]], [[Gary H. Posner]], [[Bengt I. Samuelsson]], [[Dieter Seebach]], [[Vinod K. Singh]], [[Brian Stoltz]], [[Alice Y. Ting|Alice Ting]], [[Hisashi Yamamoto]], [[Phil Baran]] and [[Jin-Quan Yu]]. A database of 580 former members and their current affiliation was developed for Corey's 80th birthday in July 2008.<ref name="ejcorey.org">{{cite web | title=Group Members: Elias James Corey | website=ejcorey.org | url=http://ejcorey.org/corey/members/members.php | access-date=22 July 2021}}</ref>

==Woodward–Hoffmann rules==
When awarded the Priestley Medal in 2004, E. J. Corey created a controversy with his claim to have inspired [[Robert Burns Woodward]] prior to the development of the [[Woodward–Hoffmann rules]]. Corey wrote:

''"On May 4, 1964, I suggested to my colleague R. B. Woodward a simple explanation involving the symmetry of the perturbed (HOMO) molecular orbitals for the stereoselective cyclobutene → 1,3-butadiene and 1,3,5-hexatriene → cyclohexadiene conversions that provided the basis for the further development of these ideas into what became known as the Woodward–Hoffmann rules."''<ref>See the E. J. Corey, Impossible Dreams tab{{cite news
  | last = Corey
  | first = E.J.
  | title = Impossible Dreams
  | pages = 2917–2919
  | publisher = JOC Perspective
  | volume=69
  | number=9
  | date=April 30, 2004
  | url = http://ejcorey.com/
  | access-date = September 10, 2010}}
</ref>

This was Corey's first public statement on his claim that starting on May 5, 1964, Woodward put forth Corey's explanation as his own thought with no mention of Corey and the conversation of May 4.  Corey had discussed his claim privately with Hoffmann and close colleagues since 1964.  Corey mentions that he made the Priestley statement ''"so the historical record would be correct"''.<ref>{{cite news|last=Johnson |first=Carolyn Y. |title=Whose idea was it? |work=Boston Globe |date=March 1, 2005 |url=http://www.boston.com/news/globe/health_science/articles/2005/03/01/whose_idea_was_it?pg=2 |access-date=September 10, 2010 |url-status=dead |archive-url=https://web.archive.org/web/20120111165854/http://www.boston.com/news/globe/health_science/articles/2005/03/01/whose_idea_was_it?pg=2 |archive-date=January 11, 2012 }}
</ref>

Corey's claim and contribution were publicly rebutted by [[Roald Hoffmann]] in the journal ''[[Angewandte Chemie]]''.  In the rebuttal, Hoffmann states that he asked Corey over the course of their long discussion of the matter why Corey did not make the issue public.  Corey responded that he thought such a public disagreement would hurt Harvard and that he would not "consider doing anything against Harvard, to which I was and am so devoted." Corey also hoped that Woodward himself would correct the historical record "as he grew older, more considerate, and more sensitive to his own conscience."<ref>{{cite journal
  | last = Hoffman
  | first = Roald
  | title = A Claim on the Development of the Frontier Orbital Explanation Electrocyclic Reactions
  | pages = 6586–6590
  | journal = Angewandte Chemie International Edition
  | volume = 43 |issue = 48 |date = December 10, 2004
  | doi = 10.1002/anie.200461440
  | pmid=15558636| doi-access = free
  }}
</ref> Woodward died suddenly of a heart attack in his sleep in 1979.

==Awards and honors==
E.J. Corey has received more than 40 major awards including the [[Linus Pauling Award]] (1973), [[Franklin Medal]] (1978), [[Tetrahedron Prize]] (1983), [[Wolf Prize in Chemistry]] (1986), [[National Medal of Science]] (1988),  [[Japan Prize]] (1989), [[Nobel Prize in Chemistry]] (1990), Golden Plate Award of the [[Academy of Achievement|American Academy of Achievement]] (1991),<ref>{{cite web|title= Golden Plate Awardees of the American Academy of Achievement |website=www.achievement.org|publisher=[[American Academy of Achievement]]|url=https://achievement.org/our-history/golden-plate-awards/#science-exploration}}</ref> Roger Adams Award (1993), and the [[Priestley Medal]] (2004).<ref name=major-awards>See the E.J. Corey, About E.J. Corey, Major Awards tab {{cite news
  | title = Compiled Works of Elias J. Corey
  | date = July 12, 2008
  | url = http://ejcorey.org/corey/about/majorawards.html
  | access-date = November 15, 2013}}
</ref> He was inducted into the [[Alpha Chi Sigma]] Hall of Fame in 1998.<ref name="alphachisigma.org"/>
As of 2008, he has been awarded 19 honorary degrees from universities around the world including [[Oxford University]] (UK), [[Cambridge University]] (UK), and [[National Chung Cheng University]].<ref>See the E.J. Corey, About E.J. Corey, Honorary Degrees tab{{cite news
  | title = Compiled Works of Elias J. Corey
  | date = July 12, 2008
  | url = http://ejcorey.org/corey/about/honorarydegress.html
  | access-date = November 15, 2013}}
</ref> In 2013, the E.J. Corey Institute of Biomedical Research (CIBR) opened in Jiangyin, Jiangsu Province, China.<ref>{{cite news
 |title        = The grand opening ceremony of E.J. Corey Institute of Biomedical Research (CIBR)
 |publisher    = E.J. Corey Institute of Biomedical Research
 |date         = June 29, 2013
 |url          = http://www.cibrnobel.org/news_show.aspx?cateid=61&newsid=71
 |access-date  = August 26, 2013
 |url-status   = usurped
 |archive-url  = https://web.archive.org/web/20150620113216/http://www.cibrnobel.org/news_show.aspx?cateid=61&newsid=71
 |archive-date = June 20, 2015
}}</ref>

Corey was elected a [[List of Fellows of the Royal Society elected in 1998|Foreign Member of the Royal Society (ForMemRS) in 1998]].<ref name=formemrs>{{cite web|archive-url=https://web.archive.org/web/20151018215239/https://royalsociety.org/people/elias-corey-11263/|archive-date=October 18, 2015|url=https://royalsociety.org/people/elias-corey-11263/|title=Professor Elias Corey ForMemRS Foreign Member|publisher=[[Royal Society]]|location=London}}</ref>

==References==
{{Reflist|30em|refs=
<ref name="acidic chromium oxidation">{{cite journal | last1 = Corey | first1 = E. J. | last2 = Boger | first2 = D. | year = 1978 | title   =Oxidative cationic cyclization reactions effected by pyridinium chlorochromate| journal = Tetrahedron Lett. | volume = 19 | issue = 28| pages = 2461–2464 | doi=10.1016/s0040-4039(01)94800-2}}</ref>
<ref name=Dauben>{{cite journal | last1 = Yang | display-authors = etal   | year = 2010 | title   =Asymmetric Total Synthesis of Caribenol A| journal = Journal of the American Chemical Society | volume = 132 | issue = 39| pages = 13608–13609 | doi = 10.1021/ja106585n | pmid = 20831198   | bibcode = 2010JAChS.13213608L }}</ref>
<ref name=PCC>{{cite journal | last1 = Corey | first1 = E.J. | last2 = Suggs | first2 = W. | year = 1975 | title   =Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds| journal = [[Tetrahedron Lett.]] | volume = 16 | issue = 31| pages = 2647–2650 | doi = 10.1016/s0040-4039(00)75204-x }}</ref>
<ref name=TBS>{{cite journal | last1 = Corey | first1 = E. J. | last2 = Venkateswarlu | first2 = A. | year = 1972 | title   =Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives| journal = [[J. Am. Chem. Soc.]] | volume = 94 | issue = 17| pages = 6190–6191 | doi = 10.1021/ja00772a043 | bibcode = 1972JAChS..94.6190C }}</ref>
<ref name=TBSPop1>{{cite journal | last1 = Mori | display-authors = etal   | year = 1998 | title   =Formal Total Synthesis of Hemibrevetoxin B by an Oxiranyl Anion Strategy| journal = J. Org. Chem. | volume = 63 | issue = 18| pages = 6200–6209 | doi=10.1021/jo980320p| pmid = 11672250   }}</ref>
<ref name=TBSPop2>{{cite journal | last1 = Furstner | display-authors = etal   | year = 2001 | title   =Alkyne Metathesis: Development of a Novel Molybdenum-Based Catalyst System and Its Application to the Total Synthesis of Epothilone A and C| journal = Chem. Eur. J. | volume = 7 | issue = 24| pages = 5299–5317 | doi=10.1002/1521-3765(20011217)7:24<5299::aid-chem5299>3.0.co;2-x| pmid = 11822430   }}</ref>
}}

==External links==
{{Commons category|E.J. Corey}}
{{wikiquote}}
*[http://www.ejcorey.org/corey/index.html Compiled Works of E.J. Corey ]
* {{Nobelprize}}
*[https://www.nobelprize.org/uploads/2018/06/corey-lecture.pdf Elias James Corey Nobel Lecture] ([[PDF]])
*[http://traffic.libsyn.com/runningthroughwalls/RTW-0048-EJCorey-Harvard-MeganBlewett_m5_29a.mp3 Podcast interview with E.J. Corey about his Lifelong Pursuit of Learning – May 30, 2018]

{{FRS 1998}}
{{Nobel Prize in Chemistry Laureates 1976-2000}}
{{1990 Nobel Prize winners}}
{{Wolf Prize in Chemistry}}
{{Japan Prize}}
{{Winners of the National Medal of Science|chemistry}}

{{Authority control}}

{{DEFAULTSORT:Corey, Elias James}}
[[Category:1928 births]]
[[Category:Living people]]
[[Category:Members of the United States National Academy of Sciences]]
[[Category:20th-century American chemists]]
[[Category:21st-century American chemists]]
[[Category:American organic chemists]]
[[Category:American people of Lebanese descent]]
[[Category:Nobel laureates in Chemistry]]
[[Category:American Nobel laureates]]
[[Category:Harvard University faculty]]
[[Category:Wolf Prize in Chemistry laureates]]
[[Category:Massachusetts Institute of Technology School of Science alumni]]
[[Category:National Medal of Science laureates]]
[[Category:Foreign members of the Royal Society]]
[[Category:University of Illinois Urbana-Champaign faculty]]
[[Category:People from Methuen, Massachusetts]]
[[Category:Lawrence High School (Massachusetts) alumni]]
[[Category:Members of the National Academy of Medicine]]
[[Category:Recipients of Franklin Medal]]