Everything about The Sharpless Epoxidation totally explained
The
Sharpless epoxidation reaction is an
enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary
allylic alcohols. 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
diethyl tartrate. Only 5-10 mol% of the catalyst in the presence of 3
Å molecular sieves (3Å MS) is necessary.
Several reviews have been published.
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.
Reaction mechanism
The Sharpless group has investigated both the reaction kinetics and the structure of the catalyst.
Further Information
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