CHIRAL 2-ACETAMIDOACRYLATES IN CONJUGATE ADDITION ASYMMETRIC ENOLATE TRAPPING REACTIONS - ASYMMETRIC-SYNTHESIS OF PHENYLALANINE

被引：21

作者：

CATIVIELA, C

DIAZDEVILLEGAS, MD

GALVEZ, JA

机构：

[1] Inst. de Ciencia de Mater. de Aragon, Departamento de Quimica Organica, Universidad de Zaragoza

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1992年 / 70卷 / 09期

关键词：

D O I：

10.1139/v92-294

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new route to the asymmetric synthesis of alpha-amino acids based on the reactivity of chiral 2-acetamidoacrylates with nucleophiles through a conjugate addition followed by diastereoselective protonation of the enolate is described. Phenylalanine precursors are obtained in excellent chemical yields (80-95%) with moderate diastereomeric excess (0-44%) through the reaction of chiral 2-acetamidoacrylates with phenylmagnesium bromide in the presence of CuI followed by diastereoselective enolate protonation.

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页码：2325 / 2328

页数：4

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