Zinc-metal promoted selective α-haloacylation and gem-bisacylation of alkyl aldehydes in the presence of chlorotrimethylsilane

被引：18

作者：

Ishino, Y

Mihara, M

Takeuchi, T

Takemoto, M

机构：

[1] Osaka Municipal Tech Res Inst, Joto Ku, Osaka 5368553, Japan

[2] Yamamoto Chem Ind Co Ltd, Wakayama 6408255, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 17期

关键词：

zinc; TMSCl; acylals; alpha-haloalkyl carboxylates;

D O I：

10.1016/j.tetlet.2004.02.159

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of a mixture of alkyl aldehydes (1) with acid chlorides (2) in the presence of zinc metal powder and a catalytic amount of chlorotrimethylsilane (TMSCl) in dichloromethane brought about highly facile and effective coupling to give selectively the corresponding alpha-haloacylation and gem-bisacylation products, alpha-haloalkyl carboxylates and 1,1-dicarboxylates (acylals), in good to excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3503 / 3506

页数：4

共 27 条

[1] Solvent free synthesis and deprotection of 1,1-diacetates over a commercially available zeolite Y as a reusable catalyst [J].