A NEW GENERAL-APPROACH TO ENANTIOMERICALLY PURE CYCLIC AND OPEN-CHAIN (R)-ALPHA,ALPHA-DISUBSTITUTED AND (S)-ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACIDS

被引：91

作者：

OBRECHT, D ^{[1
]}

SPIEGLER, C ^{[1
]}

SCHONHOLZER, P ^{[1
]}

MULLER, K ^{[1
]}

HEIMGARTNER, H ^{[1
]}

STIERLI, F ^{[1
]}

机构：

[1] UNIV ZURICH,INST ORGAN CHEM,CH-8057 ZURICH,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1992年 / 75卷 / 05期

关键词：

D O I：

10.1002/hlca.19920750522

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A wide range of cyclic and open-chain alpha,alpha -disubstituted alpha -amino acids 1a-p were prepared. The racemic N-acylated alpha,alpha -disubstituted amino acids were resolved by coupling to chiral amines 15-18 derived from (S)-phenylalanine to form diastereoisomers 19/20 or 21/22 that could be separated by crystallization and/or flash chromatography on silica gel (Scheme 3). Selective cleavage via the 1,3-oxazol-5(4H)-ones 10a-p gave the corresponding optically pure alpha,alpha -disubstituted amino-acid derivatives 11 or 12 in high yield (Scheme 3). The aboslute configurations of the alpha,alpha -disubstituted amino acids were determined from X-ray structures of the diastereoisomers 20, 21g', 22d.

引用

页码：1666 / 1696

页数：31

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