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Synfacts 2008(4): 0389-0389  
DOI: 10.1055/s-2008-1042783
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Addition of Organoboron Nucleophiles to Conjugated Alkenes

Contributor(s): Mark Lautens, Frédéric Ménard
S. Sörgel, N. Tokunaga, K. Sasaki, K. Okamoto, T. Hayashi*
Kyoto University, Japan
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

Medicinally important chiral diarylmethine subunits 3 are obtained with very high enantioselectivity by conjugate addition of boronic acids using rhodium and a chiral diene ligand previously developed by Hayashi and co-workers (Ph-bod*: Org. Lett. 2005, 7, 307). The key reaction was applied in an eight-step enantioselective synthesis of (R)-tolterodine.