ASYMMETRIC CATALYSIS .73. ENANTIOSELECTIVE DECARBOXYLATION OF METHYLPHENYLMALONIC ACID-DERIVATIVES WITH CU(I) ALKALOID CATALYSTS

被引：17

作者：

BRUNNER, H

KURZWART, M

机构：

来源：

MONATSHEFTE FUR CHEMIE | 1992年 / 123卷 / 1-2期

关键词：

DECARBOXYLATION; ENANTIOSELECTIVITY; MALONIC ACID DERIVATIVES; ALKALOIDS; CU CATALYSIS;

D O I：

10.1007/BF01045304

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methylphenylmalonic acid was decarboxylated to yield 2-phenylpropionic acid with an optical induction of 36% ee using catalytic amounts of CuCl and an excess of (+)-cinchonine in acetonitril. Methylphenylmalonic acid hemiethylester gave ethyl 2-phenylpropionate of 20% ee with catalytic amounts of CuCl and (+)-cinchonine, respectively. The tetraethylammonium salt of methylphenylmalonic acid could be decarboxylated in the presence of CuCl, (+)-cinchonine, and chiral carboxylic acids, the best result of 27% ee being obtained with malic acid.

引用

页码：121 / 128

页数：8

共 19 条

[1] The mechanism of the Hofmann reaction retention of optical activity during the reaction with (+)hydratropamide [J].