A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf

被引：40

作者：

Downey, C. Wade ^{[1
]}

Johnson, Miles W. ^{[1
]}

机构：

[1] Univ Richmond, Dept Chem, Richmond, VA 23173 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 20期

关键词：

mukaiyama aldol; silyl triflate; silyl trifluoromethanesulfonate; enol silane;

D O I：

10.1016/j.tetlet.2007.03.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A slight excess of silyl trifluoromethanesulfonate mediates a tandem enol silane formation-Mukaiyama aldol reaction in the presence of Hunig's base. Preformation of the enol silane is unnecessary for efficient reactions, which proceed in 75-97% yield for the addition of aryl methyl ketones and acetate esters to non-enolizable aldehydes. Mechanistic data suggests that free amine is crucial for full conversion. (C) 2007 Elsevier Ltd. All rights reserved.

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页码：3559 / 3562

页数：4

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