Editing Sharpless epoxidation (section)

{{Short description|Chemical reaction}}
{{Use dmy dates|date=April 2023}}
{{Reactionbox
| Name = Sharpless epoxidation
| Type = Ring forming reaction
| NamedAfter = [[Karl Barry Sharpless]]
| Section3 = {{Reactionbox Identifiers
 | OrganicChemistryNamed = sharpless-epoxidation
 | RSC_ontology_id = 0000141
}}
}}
The '''Sharpless epoxidation''' reaction is an [[enantiomer|enantioselective]] [[chemical reaction]] to prepare 2,3-epoxyalcohols from primary and secondary [[allyl alcohol|allylic alcohol]]s.  The [[oxidizing agent]] is [[tert-Butyl hydroperoxide|''tert''-butyl hydroperoxide]]. The method relies on a [[catalyst]] formed from [[Titanium isopropoxide|titanium tetra(isopropoxide)]] and [[diethyl tartrate]].<ref name = ChemRev>{{cite journal |doi=10.1021/cr040698p|title=In the Arena of Enantioselective Synthesis, Titanium Complexes Wear the Laurel Wreath|author=Diego J. Ramón and Miguel Yus|journal=Chem. Rev.|year=2006|volume=106|issue=6|pages=2126–2208|pmid=16771446}}</ref><ref>{{cite journal|author=Johnson, R. A.|author2=Sharpless, K. B.|author2-link=K. Barry Sharpless |journal=Compr. Org. Synth.|year=1991|volume=7|pages= 389–436|doi=10.1016/B978-0-08-052349-1.00196-7|title=Addition Reactions with Formation of Carbon–Oxygen Bonds: (ii) Asymmetric Methods of Epoxidation|isbn=978-0-08-052349-1}}</ref><ref>{{cite journal|author=Hüft, E. |journal=Top. Curr. Chem.|year=1993|volume=164|pages= 63–77|doi=10.1007/3-540-56252-4_25|title=Enantioselective epoxidation with peroxidic oxygen|series=Topics in Current Chemistry|isbn=978-3-540-56252-8}}</ref><ref>{{cite journal|title=Asymmetric Epoxidation of Allylic Alcohols: The Katsuki-Sharpless Epoxidation Reaction|doi=10.1002/0471264180.or048.01|author1=Katsuki, T. |author2=Martin, V. S. |journal=Org. React.|year=1996|volume=48|pages= 1–300|isbn=0471264180}}</ref><ref>{{cite journal|author=Pfenninger, A. |journal=Synthesis|year=1986|pages= 89–116|doi=10.1055/s-1986-31489|title=Asymmetric Epoxidation of Allylic Alcohols: The Sharpless Epoxidation|volume=1986|issue=2}}</ref>
[[File:Sharpless epoxidation DE.svg|center|400px|The Sharpless epoxidation]]

2,3-Epoxyalcohols can be converted into [[diol]]s, aminoalcohols, and [[ether]]s. The reactants for the Sharpless epoxidation are commercially available and relatively inexpensive.<ref name="Uetikon1986">{{cite journal|author=A. Pfenninger|journal=Synthesis |year=1986|pages= 88–116|doi=10.1055/s-1986-31489|title=Asymmetric Epoxidation of Allylic Alcohols: The Sharpless Epoxidation|volume=1986 |issue=2 }}</ref>
[[K. Barry Sharpless]] published a paper on the reaction in 1980 and was awarded the [[2001 Nobel Prize in Chemistry]] for this and related work on asymmetric [[oxidations]]. The prize was shared with [[William S. Knowles]] and [[Ryōji Noyori]].