Stereoselective Synthesis of Saturated Heterocycles via Palladium-Catalyzed Alkene Carboetherification and Carboamination Reactions

被引：202
作者：
Wolfe, John P. [1 ]
机构：
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
来源：
SYNLETT | 2008年 / 19期
关键词：
alkenes; catalysis; heterocycles; palladium; stereoselective synthesis;
D O I：
10.1055/s-0028-1087339
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of palladium-catalyzed carboetherification and carboamination reactions between aryl or alkenyl halides and alkenes bearing pendant heteroatoms is described. These transformations effect the stereoselective construction of useful heterocycles, such as tetrahydrofurans, pyrrolidines, imidazolidin-2-ones, isoxazolidines, and piperazines. The scope, limitations, and applications of these reactions are presented, and current stereochemical models are described. The mechanism of the product formation, which involves an unusual intramoleculars syn-insertion of an alkene into a palladium-heteroatom bond, is also discussed in detail.
引用
收藏
页码：2913 / 2937
页数：25
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