THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA THE ADDITION OF GRIGNARD-REAGENTS TO IMINE DERIVATIVES

被引：34

作者：

HAMON, DPG

MASSYWESTROPP, RA

RAZZINO, P

机构：

[1] Department of Organic Chemistry, University of Adelaide, Adelaide, SA 5001

来源：

TETRAHEDRON | 1992年 / 48卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)90125-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ester 8-phenylmenthyl N-Boc-glycinate 5a, undergoes free radical bromination by N-bromosuccinimide to give 8-phenylmenthyl N-Boc-bromoglycinate 8. Treatment of the bromide 8 with a variety of Grignard reagents at low temperature gave 8-phenylmenthyl (S)-N-Boc-2-alkylglycinates with high diastereoselectivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant amino acid.

引用

页码：5163 / 5178

页数：16

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