钴介导的烯烃与α,β-不饱和酮及亚胺的[3 + 2]环化反应。

Cobalt-mediated [3 + 2]-annulation reaction of alkenes with alpha,beta-unsaturated ketones and imines.

作者信息

Schomaker Jennifer M, Toste F Dean, Bergman Robert G

机构信息

Department of Chemistry, University of California, Berkeley, California 94720, USA.

出版信息

Org Lett. 2009 Aug 20;11(16):3698-700. doi: 10.1021/ol901542n.

DOI:10.1021/ol901542n

PMID:19639989

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2736344/

Abstract

The utility of cobalt dinitrosyl complexes for the [3 + 2] annulation of alkenes with unsaturated enones and ketimines has been demonstrated. Reaction of a series of cobalt dinitrosyl/alkene adducts with conjugate acceptors in the presence of Sc(OTf)(3)/LHMDS formed two new C-C bonds at the carbons alpha to the nitrosyl groups of the substrate, leading to unusual tri- and tetracycles. Retrocycloaddition of these products in the presence of norbornadiene yielded functionalized tetrasubstituted bicyclic olefins.

摘要

已证明二亚硝酰钴配合物在烯烃与不饱和烯酮和酮亚胺的[3 + 2]环化反应中的实用性。一系列二亚硝酰钴/烯烃加合物与共轭受体在Sc(OTf)₃/LHMDS存在下反应，在底物亚硝酰基α位的碳上形成了两个新的C-C键，生成了不寻常的三环和四环化合物。这些产物在降冰片二烯存在下进行逆环加成反应，得到了官能化的四取代双环烯烃。