A NEW SYNTHESIS OF ALPHA-METHYLSERINE BY NUCLEOPHILIC RING-OPENING OF N-SULFONYL AZIRIDINES

被引：45

作者：

WIPF, P

VENKATRAMAN, S

MILLER, CP

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 21期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(95)00621-I

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conversion of tritylated 2-methylglycidol to the corresponding aziridine occurs by Staudinger cyclization of the intermediate azido alcohol. After N-sulfonylation with Ses-Cl and ring-opening with benzyl alcohol, oxidation of the primary alcohol provides N,O-bisprotected alpha-methylserine directly suitable for repetitive peptide synthesis. This sequence represents a general enantioselective protocol for the synthesis of alpha-methylserine and other alpha,alpha-disubstituted amino acids.

引用

页码：3639 / 3642

页数：4

共 22 条

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