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Synfacts 2005(3): 0313-0313  
DOI: 10.1055/s-2005-921641
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Chiral Diene-Rhodium Complex Catalyzed 1,4-Addition of Arylboronic Acids

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Hayashi*, N. Tokunaga, K. Okamoto, R. Shintani
Kyoto University, Japan
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

High enantioselectivities (˜90%) were obtained in the1,4-addition of arylboronic acids to enals. The use of (R,R)-Bn-bod as the chiral diene ligand gave uniformly good yields and ee’s for a variety of α,β-unsaturated aldehyde and arylboronic acid substrates. Conditions employing KOH (10 mol%) and a MeOH-THF-H2O mixed solvent system proved critical for high regioselectivity.