N-Heterocyclic Carbene-Catalyzed Generation of α,β-Unsaturated Acyl Imidazoliums: Synthesis of Dihydropyranones by their Reaction with Enolates

被引：255

作者：

Ryan, Sarah J. ^{[1
]}

Candish, Lisa ^{[1
]}

Lupton, David W. ^{[1
]}

机构：

[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 40期

基金：

澳大利亚研究理事会;

关键词：

DIELS-ALDER REACTIONS; DIRECT ANNULATIONS; ENALS; UMPOLUNG; HOMOENOLATE; ACYLATION; ALDEHYDES; ALCOHOLS; ESTERS;

D O I：

10.1021/ja905501z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic generation of alpha,beta-unsaturated acyl imidazolium cations and enolates has been achieved, and their involvement in a Michael addition acylation sequence exploited, to provide a range of dihydropyran ones. alpha,beta-Unsaturated enol esters, or alpha,beta-unsaturated acid fluorides in association with TMS enol ethers, serve as appropriate substrates for this reaction. The transformation can also be achieved enantioselectively using catalysts derived from chiral triazolium salts.

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页码：14176 / +

页数：3

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