STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED ALPHA,BETA-UNSATURATED ESTERS AND AMIDES VIA REACTIONS OF TANTALUM ALKYNE COMPLEXES DERIVED FROM ACETYLENIC ESTERS AND AMIDES WITH CARBONYL-COMPOUNDS

被引：23

作者：

TAKAI, K

TEZUKA, M

UTIMOTO, K

机构：

[1] Department of Industrial Chemistry, Faculty of Engineering, Kyoto University, Yoshida

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 21期

关键词：

D O I：

10.1021/jo00021a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of acetylenic esters with low-valent tantalum (TaCl5 and Zn) in DME and benzene produces tantalum-alkyne complexes (not isolated), which react with carbonyl compounds regioselectively at the alpha-position of the esters to give Z isomers of trisubstituted alpha,beta-unsaturated esters in a stereoselective manner. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds at the beta-position of the amides predominantly.

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页码：5980 / 5982

页数：3

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