Highly Selective Enzymatic Kinetic Resolution of Primary Amines at 80 C: A Comparative Study of Carboxylic Acids and Their Ethyl Ester

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• 作者：Malek Nechab ; Nadia Azzi ; Nicolas Vanthuyne ; Michè ; le Bertrand ; Sté ; phane Gastaldi ; Gé ; rard Gil
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 31, 2007
• 年：2007
• 卷：72
• 期：18
• 页码：6918 - 6923
• 全文大小：127K
• 年卷期：v.72,no.18(August 31, 2007)
• ISSN：1520-6904

文摘

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Optimization of the kinetic resolution of 2-amino-4-phenyl-butane was achieved at 80 C using CAL-B-catalyzed aminolysis of carboxylic acids and their ethyl esters. The reactions carried out with longchain 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 comparedto their ester counterparts. Lauric acid led to enantiomeric excesses superior to 99.5% for both the remainingamine and the corresponding lauramide at 50% conversion (reached in 3 h). These optimized conditionswere applied to the resolution of a series of aliphatic and benzylic amines.