SIMPLE SYNTHESIS OF L-VINYLGLYCINE AND D-VINYLGLYCINE (2-AMINOBUT-3-ENOIC ACID) AND RELATED AMINO-ACIDS

被引：28

作者：

HALLINAN, KO ^{[1
]}

CROUT, DHG ^{[1
]}

ERRINGTON, W ^{[1
]}

机构：

[1] UNIV WARWICK,DEPT CHEM,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 24期

关键词：

D O I：

10.1039/p19940003537

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-step synthesis of vinylglycine 1 has been developed using a readily available starting material (but-3-enenitrile 2), based on the Neber rearrangement of the corresponding N-chloroimidate, and using cheap, convenient reagents. Also described is a convenient optical resolution of the N-tert-butoxycarbonyl derivative by papain-catalysed enantioselective esterification in a two-phase system. From the optically active amino acid, related amino acids obtained via epoxidation, dihydroxylation and cyclopropanation have been prepared. The related beta,gamma-unsaturated amino acids (E)-2-aminopent-3-enoic acid 20 and (E)-2-amino-3-methylpent-3-enoic acid 22 have been synthesised using the same approach.

引用

页码：3537 / 3543

页数：7

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