镍催化的[4+2+1]环加成反应的合成研究及机理洞察
Synthetic studies and mechanistic insight in nickel-catalyzed [4+2+1] cycloadditions.
作者信息
Ni Yike, Montgomery John
机构信息
Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA.
出版信息
J Am Chem Soc. 2006 Mar 1;128(8):2609-14. doi: 10.1021/ja057741q.
Abstract
A new nickel-catalyzed procedure for the [4+2+1] cycloaddition of (trimethylsilyl)diazomethane with alkynes tethered to dienes has been developed. A broad range of unsaturated substrates participate in the sequence, and stereoselectivities are generally excellent. Stereochemical studies provided evidence for a mechanism that involves the [3,3] sigmatropic rearrangement of divinylcyclopropanes.
摘要
已开发出一种新的镍催化方法，用于（三甲基硅基）重氮甲烷与连接到二烯上的炔烃进行[4+2+1]环加成反应。多种不饱和底物参与该反应序列，且立体选择性通常优异。立体化学研究为涉及二乙烯基环丙烷的[3,3] 迁移重排的机理提供了证据。
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2
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Org Lett. 2005 Jun 9;7(12):2405-8. doi: 10.1021/ol0506821.
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J Am Chem Soc. 2005 Feb 9;127(5):1342-3. doi: 10.1021/ja045173t.
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