THE ADDITION OF GAMMA-(TRIMETHYLSILYL)ALLYLBORONATES TO IMINES

被引：46

作者：

WUTS, PGM ^{[1
]}

JUNG, YW ^{[1
]}

机构：

[1] UNIV MICHIGAN,DEPT CHEM,ANN ARBOR,MI 48109

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 01期

关键词：

D O I：

10.1021/jo00001a067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of gamma-(trimethylsilyl)allylboronates to imines is described and compared with the addition of simple allylboronates to imines. The addition of gamma-(trimethylsilyl)allylboronates to imines is found to be more efficient than the addition of simple allylboronates to imines. The stereoselectivity is dependant upon the nature of the imine; imines derived from aromatic aldehydes give anti products and imines derived from aliphatic aldehydes give syn products. Proof of stereochemistry was established by conversion of the anti and syn derivatives to their respective Z- and E-dienes by a methylation/E-2 elimination process. With alpha-alkoxy aldehydes the reaction proceeds with excellent selectivity giving the product of Felkin-Ahn addition.

引用

页码：365 / 372

页数：8

共 65 条

[1]

[Anonymous], STEREOCHEMISTRY FUND

[2] SILICON-INDUCED FRAGMENTATIONS - STEREOSELECTIVE PREPARATION OF (Z,E)-1,4-DIENAMINE AND (Z,Z)-1,4-DIENAMINE DERIVATIVES - SYNTHESIS OF (9Z,12E)-TETRADECADIEN-1-YL ACETATE, PHEROMONE OF VARIOUS LEPIDOPTERA [J].