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

被引：11

作者：

Crotti, P

DiBussolo, V

Favero, L

Minutolo, F

Pineschi, M

机构：

[1] Dipartimento di Chimica Bioorganica, Università di Pisa, 56126 Pisa

[2] Dipto. di Chim. e Chim. Industriale, Universitè di Pisa, 56126 Pisa

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 05期

关键词：

D O I：

10.1016/0957-4166(96)00151-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(+/-)-trans-2-(Benzoylmethyl)-1-cyclohexanol 4, a gamma-hydroxy ketone (gamma-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. Copyright (C) 1996 Elsevier Science Ltd

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页码：1347 / 1356

页数：10

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