通过钯催化的烯烃碳醚化和碳胺化反应立体选择性合成饱和杂环化合物。
Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.
作者信息
Wolfe John P
机构信息
University of Michigan, Department of Chemistry, 930 N. University Avenue, Ann Arbor, Michigan, 48109-1055.
出版信息
Synlett. 2006 Nov 13;2007(4):571-582. doi: 10.1002/ejoc.200600767.
Abstract
The development of Pd-catalyzed carboetherification and carboamination reactions between aryl/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 product formation, which involves an unusual intramolecular syn-insertion of an alkene into a Pd-Heteroatom bond is also discussed in detail.
摘要
本文描述了钯催化的芳基/烯基卤化物与带有侧链杂原子的烯烃之间的碳醚化和碳胺化反应的发展。这些转化实现了有用杂环（如四氢呋喃、吡咯烷、咪唑烷-2-酮、异恶唑烷和哌嗪）的立体选择性构建。介绍了这些反应的范围、局限性和应用，并描述了当前的立体化学模型。还详细讨论了产物形成的机制，该机制涉及烯烃向钯-杂原子键的异常分子内顺式插入。
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