SYNTHESIS OF ALPHA-AMINO-ACIDS BY RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH CARBON NUCLEOPHILES

被引：70

作者：

CHURCH, NJ ^{[1
]}

YOUNG, DW ^{[1
]}

机构：

[1] UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 01期

关键词：

D O I：

10.1016/0040-4039(94)02198-K

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Excellent regiospecificity has been achieved in the reaction of carbon nucleophiles with N-para-toluenesulfonylaziridine-2-carboxylic acid (6, R = H) protected as the anion. This has been developed into a general and high yielding synthesis of optically pure alpha-amino acids containing one chiral centre. When the aziridine (20) containing a second chiral centre was used, only lithium trimethylsilylacetylide gave the desired alpha-amino acid. Reaction with higher order cuprates gave lower yields, the principal products being the protected beta-amino acids (22) and (23).

引用

页码：151 / 154

页数：4

共 32 条

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