Kinetic resolution of primary 2-methyl-substituted alcohols via Pseudomonas cepacia lipase-catalysed enantioselective acylation

被引：33

作者：

Nordin, O ^{[1
]}

Nguyen, BV ^{[1
]}

Vörde, C ^{[1
]}

Hedenström, E ^{[1
]}

Högberg, HE ^{[1
]}

机构：

[1] Mid Sweden Univ, Dept Chem & Proc Technol, SE-85170 Sundsvall, Sweden

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 03期

关键词：

D O I：

10.1039/a908023f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselectivities of lipases from Pseudomonas cepacia (PFL, Amano PS, etc.) towards a series of primary 2-methyl-substituted alcohols using vinyl acetate as the acyl donor in transesterifications in organic solvents were studied. In terms of enantioselectivity, the best results were found for 3-aryl-2-methylpropan-1-ols with enantiomeric ratios (E-values) over 100 in most cases, whereas other 3-substituted primary 2-methylpropan-1-ols generally displayed lower enantioselectivities: 3-cycloalkyl-2-methylpropan-1-ols (E approximate to 20) and 2-methylalkan-1-ols (E approximate to 10). Moving the aryl group closer or further away from the chiral centre resulted in low enantioselectivities: 2-arylpropan-1-ols (E < 10), 2-methyl-4-(2-thienyl)butan-1-ol (E = 12), 2-methyl-5-(2-thienyl)pentan-1-ol (E = 3.2) and 2-methyl-6-(2-thienyl)hexan-1-ol (E = 3.8).

引用

页码：367 / 376

页数：10

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