Editing Sharpless epoxidation (section)

==Synthetic utility==
The Sharpless epoxidation is viable with a large range of primary and secondary alkenic alcohols. Furthermore, with the exception noted above, a given dialkyl tartrate will preferentially add to the same face independent of the substitution on the [[alkene]].To demonstrate the synthetic utility of the Sharpless epoxidation, the Sharpless group created synthetic intermediates of various natural products: methymycin, [[erythromycin]], [[leukotriene]] C-1, and (+)-[[disparlure]].<ref>{{cite journal|author=Rossiter, B.|author2=Katsuki, T.|author3=[[K. Barry Sharpless|Sharpless, K. B.]] |journal=[[J. Am. Chem. Soc.]]|year=1981|volume=103|pages= 464–465| doi=10.1021/ja00392a038|title=Asymmetric epoxidation provides shortest routes to four chiral epoxy alcohols which are key intermediates in syntheses of methymycin, erythromycin, leukotriene C-1, and disparlure|issue=2|bibcode=1981JAChS.103..464R }}</ref>

[[File:Utility.png|center|Utility]]

As one of the few highly enantioselective reactions during its time, many manipulations of the 2,3-epoxyalcohols have been developed.<ref>{{cite journal|author=[[K. Barry Sharpless|Sharpless, K. B.]]|author2=Behrens, C. H.|author3=Katsuki, T.|author4=Lee, A. W. M.|author5=Martin, V. S.|author6=Takatani, M.|author7=Viti, S.M.|author8=Walker, F. J.|author9=Woodard, S. S. |journal=[[Pure Appl. Chem.]]|year=1983|volume=55|pages= 589|doi=10.1351/pac198855040589|title=Stereo and regioselective openings of chiral 2,3-epoxy alcohols. Versatile routes to optically pure natural products and drugs. Unusual kinetic resolutions|issue=4|doi-access=free}}</ref>

The Sharpless epoxidation has been used for the total synthesis of various [[saccharides]], [[terpenes]], [[leukotrienes]], [[pheromones]], and [[antibiotic]]s.<ref name="Uetikon1986" />

The main drawback of this protocol is the necessity of the presence of an [[allylic alcohol]]. The [[Jacobsen epoxidation]], an alternative method to enantioselectively oxidise alkenes, overcomes this issue and tolerates a wider array of [[functional group]]s.{{citation needed|date=December 2021}}  For specifically [[Darzens reaction|glycidic epoxides]], the Jørgensen-Córdova epoxidation avoids the need to reduce the carbonyl and then reoxidize, and has more efficient catalyst turnover.<ref>{{cite journal|url=https://www.organic-chemistry.org/Highlights/2010/05July.shtm|date=5 July 2010|first=Douglass&nbsp;F.|last=Taber|title=The Nicolaou synthesis of (+)-Hirsutellone B|journal=Organic Chemistry Highlights}}</ref>