Tetrahedron Letters

One-pot deracemisation of an enol acetate derived from a prochiral cyclohexanone

GR Allan, AJ Carnell, W Kroutil

Index: Allan, Graham R.; Carnell, Andrew J.; Kroutil, Wolfgang Tetrahedron Letters, 2001 , vol. 42, # 34 p. 5959 - 5962

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Citation Number: 18

Abstract

A one-pot method for the deracemisation of the enol acetate 1 derived from the prochiral 4, 4- disubstituted cyclohexanone 2 has been developed using the combination of Pseudomonas fluorescens lipase and potassium t-butoxide/isopropenyl acetate to give the enantiomerically pure enol acetate (S)-1 in 82% yield. Calculations based on the inherent enantioselectivity of the lipase (E) allowed an estimation of the optimum theoretical ...