SYNTHESIS OF HOMOCHIRAL L-(S)-TERT-LEUCINE VIA A LIPASE-CATALYZED DYNAMIC RESOLUTION PROCESS

被引:80
作者
TURNER, NJ [1 ]
WINTERMAN, JR [1 ]
MCCAGUE, R [1 ]
PARRATT, JS [1 ]
TAYLOR, SJC [1 ]
机构
[1] CHIROSCI LTD,CAMBRIDGE CB4 4WE,ENGLAND
关键词
D O I
10.1016/0040-4039(94)02408-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of (+/-)-2-phenyl-4-tert-butyloxazolin-5(4H)-8 with Lipozyme(R) (Mucor miehei) in toluene containing n-butanol and a catalytic amount of triethylamine resulted in a 94% yield of (S)-N-benzoyl tert-leucine butyl ester 9 (99.5% e.e.). Subsequent two step hydrolysis (Alcalase(R) followed by 6N HCl, reflux) yielded homochiral L-(S)-tert-leucine 1.
引用
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页码:1113 / 1116
页数:4
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