Lewis acid-catalyzed Meyer-Schuster reactions: methodology for the olefination of aldehydes and ketones

被引：56

作者：

Engel, Douglas A. ^{[1
]}

Lopez, Susana S. ^{[1
]}

Dudley, Gregory B. ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

TETRAHEDRON | 2008年 / 64卷 / 29期

关键词：

Meyer-Schuster; scandium(III) triflate; ethoxyacetylene; aldehyde; ketone; olefination;

D O I：

10.1016/j.tet.2008.02.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In principle, the most efficient and atom-economical means of converting an aldehyde or ketone into the homologated alpha,beta-unsaturated ester is through addition/rearrangement sequences involving acetylenic pi-bonds (Scheme 1). Implementation of such a strategy for the synthesis of a,o-unsaturated esters is presented: addition of ethoxyacetylene followed by scandium(III) triflate-catalyzed Meyer-Schuster rearrangement reaction. Stereoselectivities range from good to excellent in the formation of disubstituted alpha,beta-unsaturated esters from aldehydes (Table 3). The two-stage olefination of even the most hindered ketones proceeds with near perfect efficiency (Table 4). (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6988 / 6996

页数：9

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