A NEW ALDOL CONDENSATION OF ALPHA-ALLENIC ESTERS WITH ALDEHYDES, INCLUDING A ONE-POT SYNTHESIS OF ENYNE COMPOUNDS

被引：71

作者：

TSUBOI, S

KURODA, H

TAKATSUKA, S

FUKAWA, T

SAKAI, T

UTAKA, M

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700, Tsushima

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 22期

关键词：

D O I：

10.1021/jo00074a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DABCO-catalyzed condensations of ethyl 2,3-butadienoate (1a) with aldehydes at -6 to 25-degrees-C gave 3-hydroxy-2-vinylidenealkanoates 3 in 41-54% yields. Butyllithium-promoted condensations of 1a with aldehydes at -105 to -70-degrees-C afforded 3 in 56-67% yields. Reaction of ethyl 2,3-hexadienoate (1k) with 1-heptanal in the presence of butyllithium gave ethyl 3-hydroxy-2-(1-butenylidene)nonanoate (3k) in 64 % yield; however, when the butyllithium-promoted condensation of 1k with aldehydes was carried out at -90 to -70-degrees-C and then treated in the same pot with wet THF for 11-27 h at room temperature, ethyl (E)-2-(1-alkynyl)-2-alkenoates 7 (12-36% yields) were obtained along with 3 (14-26% yields).

引用

页码：5952 / 5957

页数：6