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环状金属化腈:立体选择性环化生成α-和β-氢化茚、十氢化萘和双环[4.3.0]十一烷。

Cyclic Metalated Nitriles: Stereoselective Cyclizations to - and -Hydrindanes, Decalins, and Bicyclo[4.3.0]undecanes.

作者信息

Fleming Fraser F, Gudipati Subramanyham

机构信息

Department of Chemistry and Biochemistry, Mellon Hall, Duquesne University, Pittsburgh PA 15282-1530, USA.

出版信息

European J Org Chem. 2008 Nov 1;2008(32). doi: 10.1002/ejoc.200800715.

Abstract

Metalated nitriles are nucleophilic chameleons whose precise identity is determined by the nature of the metal, the solvent, the temperature, and the structure of the nitrile. The review surveys the different structural types and their cyclization trajectories to show how to selectively tune the metalated nitrile geometry for stereoselective cyclizations to a variety of or hydrindanes, decalins, and bicyclo[4.3.0]undecanes.

摘要

金属化腈是亲核变色龙,其确切性质由金属的性质、溶剂、温度和腈的结构决定。本综述调查了不同的结构类型及其环化轨迹,以展示如何选择性地调节金属化腈的几何结构,从而实现对各种环戊烷、氢化茚、十氢化萘和双环[4.3.0]十一烷的立体选择性环化。

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