Palladium-catalysed enantioselective synthesis of ibuprofen

被引：15

作者：

Acemoglu, L ^{[1
]}

Williams, JMJ ^{[1
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2003年 / 196卷 / 1-2期

基金：

英国工程与自然科学研究理事会;

关键词：

palladium-catalysed allylic substitution; alpha-aryl propanoic acids; ibuprofen; ALLYLIC SUBSTITUTION-REACTIONS; (S)-2-ARYLPROPANOIC ACIDS; 2-ARYLPROPANOIC ACIDS; AMINATION; KETONES;

D O I：

10.1016/S1381-1169(02)00629-5

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A general strategy has been developed for the enantioselective synthesis of alpha-aryl propanoic acids. Palladium-catalysed asymmetric allylic substitution is used as the key step of the synthesis. Compound 2a was obtained in 95% ee from the allylic substitution reaction of 1,3-diphenylprop-2-enyl acetate la with bis(phenylsulfonyl)methane, catalysed by palladium and oxazoline ligand 9. Ozonolysis, desulfonylation followed by oxidation furnished (S)-2-phenylpropanoic acid 4a without detectable loss of enantiomeric purity. The same synthetic strategy was employed to obtain Ibuprofen 4b in 87% ee, starting from acetate 1b. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：3 / 11

页数：9

共 22 条

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