Isolable Analogues of the Breslow Intermediate Derived from Chiral Triazolylidene Carbenes

被引：121

作者：

DiRocco, Daniel A. ^{[1
]}

Oberg, Kevin M. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 14期

关键词：

DEPENDENT ENZYMATIC PATHWAYS; N-HETEROCYCLIC CARBENES; KEY INTERMEDIATE; CONDENSATIONS; GENERATION; ALDEHYDES; MECHANISM;

D O I：

10.1021/ja302031v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Since Breslow's initial report on the thiamine mode of action, the study of catalytic acyl carbanion processes has been an area of immense interest. With the advent of azolylidene catalysis, a plethora of reactivtiy has been harnessed, but the crucial nucleophilic intermediate proposed by Breslow had never been isolated or fully characterized. Herein, we report the isolation and full characterization of nitrogen analogues of the Breslow intermediate. Both stable and catalytically relevant, these species provide a model system for the study of acyl carbanion and homoenolate processes catalyzed by triazolylidene carbenes.

引用

页码：6143 / 6145

页数：3

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