LIPASE CATALYSIS IN THE OPTICAL RESOLUTION OF 2-AMINO-1-PHENYLETHANOL DERIVATIVES

被引:26
作者
KANERVA, LT
RAHIALA, K
VANTTINEN, E
机构
[1] Department of Chemistry, University of Turku
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 14期
关键词
D O I
10.1039/p19920001759
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The lipase PS- and CCL-catalysed resolution of unsubstituted and N-alkyl substituted 2-amino-1-phenylethanols with 2,2,2-trifluoroethyl butyrate or with butyric anhydride and those of the corresponding diacylated 1,2-amino alcohols with 1-alcohols in organic media have been studied. The enzymatic deacylation of diacylated 2-amino-1-phenylethanol stops at approximately 50% conversion yielding the two enantiomers with an e.e. of the order of 100%. Enantioselectivity in the case of N-alkyl substituted compounds is only somewhat lower. Also the enzymatic acylation of 2-amino-1-phenylethanol shows high enantioselectivity when the protection of the NH, group with CO2Et or CO2CH2Ph has been used. However, the direct acylation of 2-amino-1-phenylethanol or of its N-alkyl substituted derivatives are slow, the reactions stop before 40% conversion and nonenzymatic aminolysis is usually significant.
引用
收藏
页码:1759 / 1762
页数:4
相关论文
共 32 条