ELECTROCHEMICAL REDUCTION OF BENZOYLOXIRANES - STEREOSELECTIVE ELECTROSYNTHESES OF ALDOLS

被引：1

作者：

BENCHARIF, L

ROBERT, A

TALLEC, A

TARDIVEL, R

机构：

[1] CNRS,URA 704,CHIM STRUCT LAB,F-35042 RENNES,FRANCE

[2] CNRS,URA 439,ELECTROCHIM LAB,F-35042 RENNES,FRANCE

来源：

ELECTROCHIMICA ACTA | 1992年 / 37卷 / 07期

关键词：

CONTROLLED POTENTIAL ELECTROREDUCTION; CYCLIC VOLTAMMETRY; ACTIVATED EPOXIDES; ALDOLS; STEREOSELECTIVITY;

D O I：

10.1016/0013-4686(92)85063-Q

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

Electroreduction of benzoyloxiranes I has been studied in acetonitrile, containing acetic acid as a proton donor. [GRAPHICS] Voltammetric investigations show that the stability of the expected aldols II depends on the nature of the R substituent and the acidity of the electrolytic medium. Controlled potential electrolyses of I in medium of selected acidity lead to high yields of aldols II, without formation of retrocondensation products. The electrochemical ring opening is then regiospecific and moreover highly threo stereoselective.

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页码：1247 / 1251

页数：5

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