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
收藏
页码：3639 / 3642
页数：4
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