ENZYMATIC PREPARATION OF ENANTIOMERICALLY PURE ALKAN-2-OLS AND ALKAN-3-OLS BY LIPASE-CATALYZED HYDROLYSIS WITH PSEUDOMONAS-CEPACIA IN THE PRESENCE OF ORGANIC MEDIA

被引：33

作者：

NAOSHIMA, Y ^{[1
]}

KAMEZAWA, M ^{[1
]}

TACHIBANA, H ^{[1
]}

MUNAKATA, Y ^{[1
]}

FUJITA, T ^{[1
]}

KIHARA, K ^{[1
]}

RAKU, T ^{[1
]}

机构：

[1] KONAN CHEM IND CO LTD,TAKATSUKI,OSAKA 569,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 05期

关键词：

D O I：

10.1039/p19930000557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pseudomonas cepacia lipase-catalysed hydrolysis of the acetates of racemic alkan-2- and -3-ols was carried out in the presence of organic media. Good to high enantioselectivity was observed in an acetone-water solvent system, the system leading to (R)-alcohols of 80-96% ee. Enantioselectivity can be affected by the presence of the double bond in the unsaturated acetate prepared from an alkenol. The increased enantioselectivity observed for an acetone-water reaction system was utilized in the synthesis of optically active natural products possessing alkan-2-ol skeletons, such as (2R,6R,10R)-6,10,14-trimethylpentadecan-2-ol, the natural form of the sex pheromone of Corcyra cephalonica, and (R)-sulcatol, an aggregation pheromone of ambrosia beetles.

引用

页码：557 / 561

页数：5

共 28 条

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