Rhodium(I)-catalyzed [4+2+2] cycloadditions of 1,3-dienes, alkenes, and alkynes for the synthesis of cyclooctadienes

Paul A Wender; Justin P Christy

doi:10.1021/ja060878b

Rhodium(I)-catalyzed [4+2+2] cycloadditions of 1,3-dienes, alkenes, and alkynes for the synthesis of cyclooctadienes

J Am Chem Soc. 2006 Apr 26;128(16):5354-5. doi: 10.1021/ja060878b.

Authors

Paul A Wender¹, Justin P Christy

Affiliation

¹ Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.

PMID: 16620102
DOI: 10.1021/ja060878b

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%).