Asymmetric addition of chiral methylmagnesium alkoxides to benzaldehyde

被引：1

作者：

Bailey, William F. ^{[1
]}

Luderer, Mark R. ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, 55 N Eagleville Rd, Storrs, CT 06269 USA

来源：

ARKIVOC | 2010年

关键词：

Asymmetric addition; alkylmagnesium alkoxides; aggregation; Grignard; LITHIUM ACETYLIDE; REAGENTS; ALDEHYDES; KETONES;

D O I：

10.3998/ark.5550190.0011.810

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

The ability of chiral methylmagnesium alkoxides derived from enantiopure alcohols to effect asymmetric addition to benzaldehyde has been investigated. The addition to benzaldehyde of chiral methylmagnesium alkoxides prepared from (-)-borneol, (+)-menthol or (+)-N-methylpseudoephedrine afforded virtually racemic 1-phenylethanol. Equilibration of a more complex species, generated upon addition of one molar equiv of MeMgBr to various molar quantities of the dilithio salt of (+)-pseudoephedrine before addition of benzaldehyde had a dramatic effect on both the reactivity of the reagent and the enantioselectivity of the addition.

引用

页码：108 / 115

页数：8

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