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Synfacts 2008(1): 0054-0054  
DOI: 10.1055/s-2007-991486
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral Allylsilanes by Enantioselective Conjugate Addition

Contributor(s): Mark Lautens, Frédéric Ménard
R. Shintani*, Y. Ichikawa, T. Hayashi*, J. Chen, Y. Nakao, T. Hiyama*
Kyoto University, Japan
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

The instability of alkenylboronic acids has prevented their widespread use in asymmetric conjugate addition. The authors expanded the initial report of Rh(I)-catalyzed arylboronic acid addition to β-silyl enones to make use of Hiyama’s reagents 2 as alkenyl nucleophile precursor (Y. Nakao, H. Ima­naka, A. K. Sahoo, A. Yada, T. Hiyama J. Am. Chem. Soc. 2005, 127, 6952).