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Synfacts 2009(7): 0765-0765  
DOI: 10.1055/s-0029-1217275
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Ligand Control in Gold-Catalyzed Cycloadditions of Allene-Dienes

Contributor(s): Mark Lautens, David A. Candito
P. Mauleón, R. M. Zeldin, A. Z. González, F. D. Toste*
University of California, Berkeley, USA
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

The authors demonstrate a dramatic ligand effect on the gold-catalyzed cycloaddition of allene-dienes whereby selection between formal [4+2] and [4+3] cycloaddition pathways can be accomplished by choice of an appropriate ligand. The process takes place stereospecifically to provide a single diastereomer.