Microwave-assisted cleavage of Weinreb amide for carboxylate protection in the synthesis of a (R)-3-hydroxyalkanoic acid

被引：27

作者：

Jaipuri, FA

Jofre, MF

Schwarz, KA

Pohl, NL ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

[2] Iowa State Univ, Inst Plant Sci, Ames, IA 50011 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 21期

关键词：

(R)-3-hydroxyalkanoic acids; chirality; Weinreb amide; microwaves; chiral building blocks; Wittig reaction;

D O I：

10.1016/j.tetlet.2004.03.148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile route for the modular synthesis of (R)-3-hydroxyalkanoic acids, constituents of the naturally biodegradable poly(3-hydroxyalkanoate) polymers, and its application to the synthesis of (R)-3-hydroxydecanoic acid is described. Key steps include a microwave-assisted catalytic transfer hydrogenation and a facile microwave-assisted hydrolysis of an N-methoxy-N-methyl (Weinreb) amide, which enhances the practicality of this protecting group for carboxylic acids. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4149 / 4152

页数：4

共 25 条

[21] A β-lactone-based strategy applied to the total synthesis of (8S,21S,22S,23R)- and (8R,21S,22S,23R)-okinonellin B [J].