Stereocontrolled synthesis of all four stereoisomers of fully protected 2-amino-3-hydroxypentanoic acid from imines derived from D-glyceraldehyde

被引：12

作者：

Badorrey, R ^{[1
]}

Cativiela, C ^{[1
]}

Díaz-de-Villegas, MD ^{[1
]}

Gálvez, JA ^{[1
]}

机构：

[1] Univ Zaragoza, Fac Ciencias, Dept Quim Organ, Inst Ciencia Mat Aragon,CSIC, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 49期

关键词：

addition reactions; amino acids and derivatives; asymmetric synthesis; Grignard reagents; imines;

D O I：

10.1016/S0040-4020(99)00880-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Benzylimines derived from conveniently protected (R)-glyceraldehyde underwent diastereoselective phenylmagnesium bromide addition to afford the corresponding aminodiols, whose absolute configuration at the newly formed stereogenic carbon depends on the O-protecting group. These compounds can be easily transformed into optically pure N-tert-butoxycarbonyl- 1-phenyl-2,3-epoxy-1-propylamines, which are key intermediates in the synthesis of 2-tert-butoxycarbonylamino-3-acetyloxypentanoates of erythro and three configuration. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：14145 / 14160

页数：16

共 76 条

[1] Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis [J].