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
收藏
页码：195 / 202
页数：8
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