Efficient application of lipase-catalyzed transesterification to the resolution of γ-hydroxy ketones

Article abstract of DOI:10.1016/0957-4166(96)00151-6

(±)-trans-2-(Benzoylmethyl)-1-cyclohexanol 4, a γ-hydroxy ketone (γ-HK) obtained from the Sc(OTf)₃-catalyzed addition reaction of lithium enolate 1 with cyclohexene oxide 2, was very efficiently resolved into (+)-(1S,2R)-4 and acetate (-)-(1R,2S)-6 [ee >99% for both (+)-4 and (-)-6] by supported lipase PS-catalyzed enantioselective transesterification. The enantioselective Sc(OTf)₃-catalyzed addition of enolate 1 to propene oxide (+)-(R)-3 and (-)-(S)-3 is also described.