Synfacts 2011(4): 0395-0395  
DOI: 10.1055/s-0030-1259649
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Conjugated Addition of Vinylaluminums to Cyclic Enones

Contributor(s): Mark Lautens, Norman Nicolaus
T. L. May, J. A. Dabrowski, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
Further Information

Publication History

Publication Date:
18 March 2011 (online)


The development of transition-­metal-catalyzed enantioselective reactions allowing the formation of quaternary stereogenic centers is a challenging task. Herein, the authors report a highly enantioselective conjugated addition of Si-substituted vinylaluminum reagents to five- and six-membered cyclic β-substituted enones of type 1. A chiral bidentate NHC-copper complex has been identified to facilitate the desired transformation of 1 into 2 with good to excellent yields and enantioselectivities.