Steric factors direct Baylis-Hillman and aldol reactions in titanium tetrachloride mediated coupling between α-keto esters and cyclohex-2-enone derivatives

被引：54

作者：

Basavaiah, D ^{[1
]}

Sreenivasulu, B ^{[1
]}

Rao, AJ ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 15期

关键词：

D O I：

10.1021/jo0342424

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The titanium tetrachloride mediated reaction of a-keto esters with 5,5-dimethylcyclohex-2-enone provides the corresponding Baylis-Hillman adducts exclusively whereas a similar reaction of a-keto esters with cyclohex-2-enone furnishes the corresponding aldol adducts (with high syn-diasteroe-selectivity) as the major product (along with the Baylis-Hillman adducts as the minor product), thus clearly demonstrating the role of the steric factors in directing the reaction pathway.

引用

页码：5983 / 5991

页数：9