(±)-Trans-2-(benzoylmethyl)-1-cyclohexanol, a γ-hydroxy ketone obtained from the Sc(OTf)3-catalyzed addn. reaction of acetophenone lithium enolate (1) with cyclohexene oxide, was very efficiently resolved into (+)-(1S,2R)-2-(benzoylmethyl)-1-cyclohexanol and the (-)-(1R,2S)-acetate (ee >99%) by supported lipase PS-catalyzed enantioselective transesterification. The enantioselective Sc(OTf)3-catalyzed addn. of enolate 1 to (+)-(R)- and (-)-(S)-propene oxide is also described.
Efficient application of lipase-catalyzed transesterification to the resolution of gamma-hydroxy ketones
CROTTI, PAOLO;DI BUSSOLO, VALERIA;FAVERO, LUCILLA;MINUTOLO, FILIPPO;PINESCHI, MAURO
1996-01-01
Abstract
(±)-Trans-2-(benzoylmethyl)-1-cyclohexanol, a γ-hydroxy ketone obtained from the Sc(OTf)3-catalyzed addn. reaction of acetophenone lithium enolate (1) with cyclohexene oxide, was very efficiently resolved into (+)-(1S,2R)-2-(benzoylmethyl)-1-cyclohexanol and the (-)-(1R,2S)-acetate (ee >99%) by supported lipase PS-catalyzed enantioselective transesterification. The enantioselective Sc(OTf)3-catalyzed addn. of enolate 1 to (+)-(R)- and (-)-(S)-propene oxide is also described.File in questo prodotto:
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