Rhodium(I)-Catalyzed [4+2+2] Cycloadditions of 1,3-Dienes, Alkenes, and Alkynes for the Synthesis of Cyclooctadienes

Paul A. Wender* and Justin P. Christy
Departments of Chemistry and of Molecular Pharmacology, Stanford University, Stanford, California 94305-5080
J. Am. Chem. Soc., 2006, 128 (16), pp 5354–5355
DOI: 10.1021/ja060878b
Publication Date (Web): April 1, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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The first [4+2+2] cycloadditions involving terminal alkynes and diene-enes, including a fully intramolecular example, are reported resulting in the formation of cyclooctadienes using [RhCl(CO)2]2 (5 mol %) treated with AgSbF6 (10 mol %) as a precatalyst. The reaction is general for a variety of terminal alkynes, as well as variously substituted diene-enes (yields up to 88%).

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History

  • Published In Issue April 26, 2006
  • Received February 8, 2006

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