J. Am. Chem. Soc., 128 (16), 5354 -5355, 2006. 10.1021/ja060878b S0002-7863(06)00878-X
Web Release Date: April 1, 2006

Copyright © 2006 American Chemical Society

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

wenderp@stanford.edu

Received February 8, 2006

Abstract:

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%).

Download the full text: PDF | HTML