Journal
TETRAHEDRON
Volume 69, Issue 39, Pages 8516-8526Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.06.106
Keywords
Allenes; Grignard reagents; Dzhemilev reaction; Homogeneous catalysis; 1Z,5Z-Dienes
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Funding
- Russian Foundation for Basic Research [11-03-97001, 12-03-31083, 13-00-40029]
- Federal Agency for Education [02.740.11.0631]
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An efficient method for the synthesis of valuable N-, O-, and Si-containing 1Z,5Z-diene compounds was developed. The method comprises Cp2TiCl2-catalyzed homo- and cross-cyclomagnesiation of 1,2-dienes by Grignard reagents (RMgR') to give 2,5-dialkylidenemagnesacyclopentanes in up to 96% yield. This approach was successfully used in the synthesis of 5Z,9Z-dienoic acids, precursors of acetogenins and insect pheromones. (C) 2013 Elsevier Ltd. All rights reserved.
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