SYNTHESIS OF A CHIRAL SERINE ALDEHYDE EQUIVALENT AND ITS CONVERSION TO CHIRAL ALPHA-AMINO-ACID DERIVATIVES

被引：94

作者：

BLASKOVICH, MA ^{[1
]}

LAJOIE, GA ^{[1
]}

机构：

[1] UNIV WATERLOO,DEPT CHEM,WATERLOO N2L 3G1,ONTARIO,CANADA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 12期

关键词：

D O I：

10.1021/ja00065a010

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a new methodology for the synthesis of chiral nonproteinaceous alpha-amino acids, which involves protection of the carboxyl group of serine as a cyclic ortho ester. This reduces the acidity of the alpha-proton, allowing for oxidation of the side chain of serine to an aldehyde without racemization. A variety of carbonyl addition reactions, such as Grignard, Reformatsky, and Wittig additions, can then be carried out, leading to a wide range of amino acids. Very good stereocontrol is achieved, allowing for the selective synthesis of all four diastereomers of beta-hydroxy-alpha-amino acids. The method readily allows for stereospecific incorporation of both C and H isotopes in amino acid side chains.

引用

页码：5021 / 5030

页数：10

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