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Synfacts 2009(3): 0288-0288  
DOI: 10.1055/s-0028-1087748
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed 1,4-Addition of Boronic Acids to α,β-Unsaturated Ketones

Contributor(s): Mark Lautens, Jacki Kitching
R. Shintani*, Y. Ichikawa, K. Takatsu, F.-X. Chen, T. Hayashi*
Kyoto University, Japan
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

The use of chiral dienes as ligands in transition-metal-catalyzed asymmetric reactions has received considerable attention. The application of new C 2-symmetric chiral diene ligands to the rhodium-catalyzed 1,4-addition of boronic acids to α,β-unsaturated ketones is described. The ligands are based on a 3,7-disubstituted bi­cycle[3.3.1]nona-2,6-diene framework and are ­reported to provide a different chiral environment from existing chiral dienes.

Reviews: J. B. Johnson, T. Rovis Angew. Chem. Int. Ed. 2008, 47, 840; C. Defieber, H. Grütz­macher, E. M. Carreira Angew. Chem. Int. Ed. 2008, 47, 4482.