Exclusive gamma-regio functionalization of crotonaldehyde using gamma-trimethylsilyl crotonaldimine. Application to the one pot synthesis of conjugated dienals.

被引：25

作者：

Bellassoued, M

Salemkour, M

机构：

[1] Univ. Pierre et Marie Curie, Lab. de Synt. Organometallique, Associé au CNRS, 75252 Paris Cedex 05

来源：

TETRAHEDRON | 1996年 / 52卷 / 13期

关键词：

D O I：

10.1016/0040-4020(96)00165-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cesium fluoride mediated reaction of gamma-trimethylsilyl N-tert-butyl crotonaldimine 9 with a wide range of aldehydes takes place in DMSO at room temperature and affords exclusive gamma-regio functionalized products. Heating (rt to 100 degrees C) the delta-silyloxy imines 11 thus obtained leads, after very mild hydrolysis of the tert-butylimine function, to the conjugated dienals 14 in good yields and with excellent (E,E)-selectivities.

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页码：4607 / 4624

页数：18

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