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Synfacts 2005(3): 0320-0320  
DOI: 10.1055/s-2005-916130
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Bicyclic Cyclohexadienes via Rh-Catalyzed Carbocyclization

Contributor(s): Mark Lautens, Andrew Martins
P. A. Evans*, K. W. Lai, J. R. Sawyer
Indiana University, Bloomington, USA
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

Enantioselective versions of the metal-catalyzed [2+2+2] carbocyclization of 1,6-enynes and internal alkynes have not been reported prior to this work. Evans reports that in the presence of [RhCl(COD)2], (S)-Xyl-P-Phos, and AgBF4, 1,6-enynes are coupled with internal alkynes to afford bicyclic cyclohexadienes with high enantioselectivity and good to excellent re­gioselectivity. Neither the yield, ee, nor the regio­selectivity of the reaction varies greatly as a function of the electronic nature of the reagents.