Sharpless epoxidation

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The Sharpless epoxidation reaction is an enantioselective reaction to prepare 2,3-epoxyalcohols from primary and secondary allyl alcohols. This reaction gives good yields and enantioselectivities over a broad range of substrates.

Epoxides can be easily converted into dialcohols, aminoalcohols or ethers, so formation of chiral epoxides is a very important step in the synthesis of natural products.

The oxidizing agent is t-butylperoxide. Enantioselectivity is achieved by a catalyst formed from titanium tetra(isopropoxide) and tartrate ester.

K. Barry Sharpless shared the Nobel prize in 2001 for his work on asymmetric oxidations. The prize was shared with William S. Knowles and Ryoji Noyori.de:Sharpless-Epoxidierung nl:Sharpless epoxidatie ja:シャープレス酸化