Kinetic resolution of trans-2-(1-pyrazolyl)cyclohexan-1-ol catalyzed by lipase B from Candida Antarctica

被引：24

作者：

Barz, M ^{[1
]}

Herdtweck, E ^{[1
]}

Thiel, WR ^{[1
]}

机构：

[1] TECH UNIV MUNICH, INST ANORGAN CHEM, D-85747 GARCHING, GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 06期

关键词：

D O I：

10.1016/0957-4166(96)00205-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of epoxycyclohexane with pyrazole gives trans-2-(1-pyrazolyl)cyclohexan-1-ol rac-1 in high yields. Rac-1 forms dimers in the solid state by linking one (1R,2R)- and one (1S,2S)-enantiomer via strong intermolecular H-bonds. In the presence of the immobilized lipase B of candida antarctica yeast, rac-1 is acylated enantioselectively with isopropenylacetat acting as the acylating agent. Crystallisation of the reaction mixture gives enantiomerically pure (1S,2S)-1, which forms a helical structure in the solid state. The absolute configuration of this alcohol was examined by X-ray structure analysis of the esterification product with 5-oxo-(2R)-(trichloromethyl)-1,3-dioxolane-(4S)-acetylchloride 3. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1717 / 1722

页数：6

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