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Synfacts 2006(3): 0239-0239  
DOI: 10.1055/s-2006-931952
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Intramolecular [4+2] Cycloadditions of Alkynyl Halides

Contributor(s): Mark Lautens, Josephine Yuen
W.-J. Yoo, A. Allen, K. Villeneuve, W. Tam*
University of Guelph, Canada
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

The first example of a rhodium-catalyzed intramolecular [4+2] cycloaddition of diene-tethered alkyne halides is described. Yields were very good and single stereoisomers were obtained. Both the thermal and rhodium-catalyzed [4+2] cycloadditions were described. For the thermal reaction, longer tethers were unsuccessful, but the rhodium-catalyzed reaction generated both five- and six-membered rings. Alkynyl chlorides, bromides and iodides were described with yields being slightly poorer for the iodides.