Synfacts 2011(4): 0402-0402  
DOI: 10.1055/s-0030-1259668
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Hydroboration of α-Substituted Styrenyl Derivatives

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
C. Mazet*, D. Gérard
University of Geneva, Switzerland
Further Information

Publication History

Publication Date:
18 March 2011 (online)


1,1-Disubstituted olefins represent a group of challenging substrates for asymmetric transformations, generally providing lower stereoselectivities than other alkenes. Using these starting materials, the rhodium-mediated β-hydroboration was found to be suppressed by the α-pathway. In this paper, iridium catalysis is used to accomplish the enantioselective β-hydroboration of terminal alkenes with high catalytic activity, perfect regioselectivity, and ee values up to 92%. The catalytic asymmetric hydroboration remains one of the long-standing problems, which can hopefully be solved via iridium catalysis.