Synfacts 2010(1): 0080-0080  
DOI: 10.1055/s-0029-1218470
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds

Contributor(s): Mark Lautens, Stephen G. Newman
T. Shiomi, T. Adachi, K. Toribatake, L. Zhou, H. Nishiyama*
Nagoya University, Japan
Further Information

Publication History

Publication Date:
21 December 2009 (online)

Significance

The introduction of boronate esters β to carbonyls cannot be achieved by classical asymmetric hydroboration. Metal-catalyzed addition of boron reagents to α,β-unsaturated carbonyl compounds has become a reliable method to introduce this functionality. In this report, the authors utilize their previously developed chiral rhodium(III) catalysts to achieve asymmetric conjugate addition of a diboron reagent to obtain enantio­enriched β-boryl carbonyl derivatives.