Tetrahedron: Asymmetry

Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes

A Steinreiber, SF Mayer, R Saf, K Faber

文献索引：Steinreiber, Andreas; Mayer, Sandra F.; Saf, Robert; Faber, Kurt Tetrahedron Asymmetry, 2001 , vol. 12, # 10 p. 1519 - 1528

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被引用次数: 29

摘要

Asymmetric biohydrolysis of trialkyl oxiranes (±)-1a–3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols 1b–3b in up to 97% enantiomeric excess (ee) as the sole product. The mechanism of this enantioconvergence was investigated by 18O- labelling experiments and it was found that both enantiomers were hydrolysed with ...