Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation

被引：19

作者：

Egri, G

BaitzGacs, E

Poppe, L

机构：

[1] TECH UNIV BUDAPEST,DEPT ORGAN CHEM TECHNOL,H-1521 BUDAPEST,HUNGARY

[2] HUNGARIAN ACAD SCI,CENT RES INST CHEM,H-1525 BUDAPEST,HUNGARY

来源：

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

关键词：

D O I：

10.1016/0957-4166(96)00161-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzyme and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1437 / 1448

页数：12

共 26 条

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