THE HIGHLY SYN-SELECTIVE MICHAEL REACTION OF ENAMINES WITH 2-(1-ALKENYL)-1,3-DIOXOLAN-2-YLIUM CATIONS GENERATED FROM 2,2-DIMETHOXYETHYL 2-ALKENOATES INSITU

被引：20

作者：

MACHIDA, S ^{[1
]}

HASHIMOTO, Y ^{[1
]}

SAIGO, K ^{[1
]}

INOUE, J ^{[1
]}

HASEGAWA, M ^{[1
]}

机构：

[1] UNIV TOKYO,FAC ENGN,DEPT SYNTHET CHEM,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON | 1991年 / 47卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(01)80900-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,2-Dimethoxyethyl 2-alkenoates are easily transformed into 2-(1-alkenyl)-1,3-dioxolan-2-ylium cations in situ on the action of titanium tetrachloride, which react with enamines to predominantly give syn Michael adducts in good yields. This is the first example of such a high syn-selectivity for the Michael reaction of alpha,beta-unsaturated ester derivatives with ketone enolate equivalents.

引用

页码：3737 / 3752

页数：16

共 57 条

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