Kinetic resolution of 3-hydroxycyclohexanone using different lipases

A new approach to enantiomerically enriched cyclic β-hydroxy ketones was developed. 3-Hydroxycyclohexanone was successfully resolved using lipase catalyzed transesterification. Among the lipases screened PFL, PCL, and PPL-II gave 57%, 39%, and 25% yield of the (R)-3-oxocyclohexyl acetate with 52%, 75%, and 91% ee. The PPL-II gave the highest E-value (32). The absolute configuration of the product was determined by comparison with the literature data.

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(R)-3-(tert-Butyldimethylsiloxy) cyclohexanoneC12H24O2Ee = 94%[α]D25=+4.2 (c 0.96, CHCl3)Source of chirality: PPL-II catalyzed kinetic resolutionAbsolute configuration: (R)