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Synfacts 2006(12): 1252-1252  
DOI: 10.1055/s-2006-955642
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rh(I)-Catalyzed Asymmetric Allylic Substitution with Boronic Acids

Contributor(s): Mark Lautens, Yann Béthuel
F. Ménard, T. M. Chapman, C. Dockendorff, M. Lautens*
University of Toronto, Canada
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

The authors report a C-C coupling reaction between a simple meso-cyclic dicarbonate and a boronic acid to generate optically active cyclopentenol derivatives. The Rh(I) catalyst system allowed the asymmetric allylic substitution (AAS) with hard boronic acid nucleophiles that are air- and moisture-tolerant. The use of aryl nucleophiles complements the previous asymmetric Cu(II) variant to introduce alkyl groups (F. López, A. W. van Zijl, A. J. Minnaard, B. L. Feringa Chem. Commun. 2006, 409-411). The reaction showed reliably high enantioselectivity, regardless of the substitution of the aromatic ring.