Highly selective enzymatic kinetic resolution of primary amines at 80 °C:: A comparative study of carboxylic acids and their ethyl esters as acyl donors
Highly selective enzymatic kinetic resolution of primary amines at 80 °C:: A comparative study of carboxylic acids and their ethyl esters as acyl donors
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DOI：
10.1021/jo071069t
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发表时间：
2007-08-31
影响因子：
3.6
通讯作者：
Gil, Gerard
中科院分区：
文献类型：
--
作者：
Nechab, Malek;Azzi, Nadia;Gil, Gerard
采用CAL-B催化羧酸及其乙酯的氨解反应，在80 ℃下实现了2-氨基-4-苯基丁烷动力学拆分的优化。以长链酯和相应的酸作为酰基供体进行的反应具有非常高的对映选择性。羧酸作为酰化剂的使用导致显着的加速反应速率相比，其酯对应物。月桂酸导致对映体过量上级为99.5%的剩余的胺和相应的月桂酰胺在50%的转化率（在3小时内达到）。这些优化的条件被应用于一系列的脂肪胺和苄胺的拆分。
Optimization of the kinetic resolution of 2-amino-4-phenyl-butane was achieved at 80 degrees C using CAL-B-catalyzed aminolysis of carboxylic acids and their ethyl esters. The reactions carried out with long chain esters and the corresponding acids as acyl donors proceeded with remarkably high enantioselectivity. The use of carboxylic acids as acylating agents led to a marked acceleration of the reaction rate compared to their ester counterparts. Lauric acid led to enantiomeric excesses superior to 99.5% for both the remaining amine and the corresponding lauramide at 50% conversion (reached in 3 h). These optimized conditions were applied to the resolution of a series of aliphatic and benzylic amines.