4.4 Article

Novel Mg-organic reagents in organic synthesis. Cp2TiCl2 catalyzed intermolecular cyclomagnesiation of cyclic and acyclic 1,2-dienes using Grignard reagents

Journal

TETRAHEDRON
Volume 64, Issue 44, Pages 10188-10194

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.08.041

Keywords

Metallacycles; Cyclomagnesiation; Allenes; Homogeneous catalysis; Titanium; Dzhemilev reaction

Funding

  1. Russian Foundation [08-03-00789]
  2. Russian Science Support Foundation [08-03-00789, MC-1039.2007.3, Sci.Sh.-2349.2008.3]

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High-yield (> 80%) catalytic intermolecular cyclomagnesiation of cyclic and acyclic allenes with the aid of Grignard reagents has been realized in the presence of Cp2TiCl2. The synthesized unsaturated bi- and tricyclic organomagnesium compounds (OMC) have been successfully converted in situ into thiophenes, unsaturated ketones, cyclic and acyclic hydrocarbons with high regio- and stereoselectivity. (c) 2008 Elsevier Ltd. All rights reserved.

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