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

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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

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%).

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

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Communication

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

Abstract

Available Supporting Information for This Article

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SciFinder Links

History

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Related Content

Rhodium(I)-Catalyzed [2+2], [2+2+2], and [2+2+2+2] Cycloadditions of Dienes or Alkynes with a Bis-ene

Suzuki−Miyaura Coupling of Aryl Carbamates, Carbonates, and Sulfamates

Transition Metal-Catalyzed Intermolecular [5+2] and [5+2+1] Cycloadditions of Allenes and Vinylcyclopropanes

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