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Synfacts 2006(5): 0482-0482  
DOI: 10.1055/s-2006-934440
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Conjugate Additions of Boronic Acids to Enones

Contributor(s): Hisashi Yamamoto, Matthew Boxer
K. Vandyck, B. Matthys, M. Willen, K. Robeyns, L. Van Meervelt, J. Van der Eycken*
Ghent University, Belgium
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Publikationsdatum:
21. April 2006 (online)

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Significance

This paper presents a new chiral bisphosphine ligand that was shown to be effective for rhodium-catalyzed conjugate addition of boronic acids. A four-step procedure starting from racemic 2,5-norbornadione (involving resolution with (R,R)-2,3-diphenylaminocarbonyl tartaric acid provides a new chiral bisphosphine architecture. The conjugate addition reaction has a wide substrate scope of various aryl boronic acids and ­acceptors ranging from 5-7-membered enones that all gave high yields and high enantioselectivities.