Three-Component Coupling Sequence for the Regiospecific Synthesis of Substituted Pyridines

被引：91

作者：

Chen, Ming Z. ^{[2
]}

Micalizio, Glenn C. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, Jupiter, FL 33458 USA

[2] Scripps Res Inst, Kellogg Sch Sci & Technol, Jupiter, FL 33458 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 02期

基金：

美国国家卫生研究院;

关键词：

DERIVATIVES; IMINES;

D O I：

10.1021/ja2105703

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A de novo synthesis of substituted pyridines is described that proceeds through nucleophilic addition of a dithiane anion to an alpha,beta-unsaturated carbonyl followed by metallacycle-mediated union of the resulting allylic alcohol with preformed trimethylsilane-imines (generated in situ by the low-temperature reaction of lithium hexamethyldisilazide with an aldehyde) and Ag(I)- or Hg(II)-mediated ring closure. The process is useful for the convergent assembly of di- through penta-substituted pyridines with complete regiochemical control.

引用

页码：1352 / 1356

页数：5

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