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Synfacts 2005(3): 0320-0320
DOI: 10.1055/s-2005-916130
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
P. A. Evans*, K. W. Lai, J. R. Sawyer
Indiana University, Bloomington, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2005 (online)
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.