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

A one-pot method for the deracemisation of the enol acetate I derived from the prochiral 4,4-disubstituted cyclohexanone 2 has been developed using th e combination of Pseudomonas fluorescens lipase and potassium t-butoxide/is opropenyl acetate to give the enantiomerically pure enol acetate (S)-1 in 8 2% yield. Calculations based on the inherent enantioselectivity of the lipa se (E) allowed an estimation of the optimum theoretical conversion for each enzyme step prior to recycling the ketone. (C) 2001 Elsevier Science Ltd. All rights reserved.