摘要
介绍了一种简单的制备 (1R,3S) - 3-氨基 - 1-环己烷羧酸的方法。以环己烷 - 1,3-二羧酸的顺反混合物为原料 ,经过关环得顺式的酸酐 ,然后酯化 ,在脂肪酶 AY- 30的作用下进行去对称性水解 ,得光学活性的环己烷 - 1,3-二羧酸的单乙酯产物 ,经过改进的 Curtis重排反应后 ,羧酸基团转变为氨基。然后经过酯水解、去保护基团 ,得到光学纯的 (1R,3S) - 3-氨基 - 1-环己烷羧酸。
A straightforward way to (1R,3S)-3-amino-1-cyclohexanecarboxylic acid was described. Cis and trans mixture of cyclohexane-(1,3)-dicarboxylic acid gave cis-cyclohexane-(1,3)-dicarboxylic anhydride, which was converted to cis-cyclohexane-(1,3)-dicarboxylic acid diester. After enzymatic hydrolytic desymmetrization with lipase AY-30cis-(1,3)-cyclohexanedicarboxylic acid monoester was obtained in high e.e., which was rearranged via a modified Curtis-type reaction to give 3-(t-butoxycarbonyl)amino-1-cyclohexane carboxylic acid. The obtained N-Boc protected amino ester gave rise to the desired optical pure 3-amino-1-cyclohexane carboxylic acid through hydrolyzation and deprotection. The absolute configuration and enantiomeric purity of the product were confirmed by comparing with the reported specific rotation value.
出处
《化学通报》
CAS
CSCD
北大核心
2004年第12期934-937,共4页
Chemistry
关键词
环己烷羧酸
二羧酸
氨基
乙酯
制备
水解
酸酐
基团
重排反应
光学活性
Cyclohexane-(1,3)-dicarboxylic acid, Cis-3-amino-1-cyclohexane carboxylic acid, Hydrolytic desymmetrization
