Hetero Diels-Alder vs Mukaiyama aldol pathways in the reaction of monoactivated dienes and aldehydes. A Lewis acid study

被引：22

作者：

Mujica, MT ^{[1
]}

Afonso, MM ^{[1
]}

Galindo, A ^{[1
]}

Palenzuela, JA ^{[1
]}

机构：

[1] UNIV LA LAGUNA,INST BIOORGAN,E-38026 LA LAGUNA,SPAIN

来源：

TETRAHEDRON | 1996年 / 52卷 / 06期

关键词：

D O I：

10.1016/0040-4020(95)01031-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of Lewis acid on the reaction of 2-monoactivated dienes and aldehydes was studied searching for more general reaction conditions than those previously published. It was found that BF3-OEt(2) in diethyl ether gave the best yields of Diels-Alder adducts with good endo/exo selectivities. The Mukaiyama aldol-Michael cyclization pathway which has been reported to occur with this Lewis acid in the reaction of diactivated dienes, does not seem to operate with the monoactivated ones. Other Lewis acids gave good yields of silylated aldol products, and a crossover experiment showed that the recently proposed silatropic-ene pathway does not occur under the conditions used.

引用

页码：2167 / 2176

页数：10

共 15 条

[1]

BOGER DL, 1987, HETERO DIELSALDER ME, P105

[2]

BRANDES A, 1994, SYNLETT, V9, P745

[3] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].