Stereoselective 1,3-Insertions of Rhodium(II) Azavinyl Carbenes

被引：193

作者：

Chuprakov, Stepan ^{[1
]}

Worrell, Brady T. ^{[1
]}

Selander, Nicklas ^{[1
]}

Sit, Rakesh K. ^{[1
]}

Fokin, Valery V. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 01期

基金：

瑞典研究理事会; 美国国家科学基金会; 美国国家卫生研究院;

关键词：

H INSERTION REACTIONS; RH-CATALYZED TRANSANNULATION; TERMINAL ALKYNES; RING EXPANSION; REACTIVITY; REARRANGEMENTS; CONVERSION; KETONES;

D O I：

10.1021/ja408185c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereo-selectivity. Utilizing the distinctive functionality installed through these reactions, a number of subsequent rearrangements and cyclizations expand the repertoire of valuable organic building blocks constructed by reactions of transition-metal carbene complexes, including a-allenyl ketones and amino-substituted heterocycles.

引用

页码：195 / 202

页数：8

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