Sharpless epoxidation
The
Sharpless epoxidation reaction is an
enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary
allyl alcohols.
[Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974. ()][Johnson, R. A.; Sharpless, K. B. Comp. Org. Syn. 1991, 7, 389-436. (Review)][Hüft, E. Top. Curr. Chem. 1993, 164, 63-77. (Review)] This reaction gives good yields and enantioselectivities over a broad range of substrates.
The oxidizing agent is t-butylperoxide. Enantioselectivity is achieved by a catalyst formed from titanium tetra(
isopropoxide) and
tartrate ester.
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.
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.
