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Synfacts 2006(8): 0794-0794  
DOI: 10.1055/s-2006-941954
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective α-Silylation of Enones

Contributor(s): Mark Lautens, Andrew Martins
M. Ge, E. J. Corey*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

In the presence of a chiral, proline-based Rh(II) catalyst, easily synthesized α-diazo­enones can be hydrosilylated enantioselectively to the corresponding α-silylenone in moderate to good yield and with good to very good enantioselectivity. Interestingly, when the opposite-antipode catalyst was used, lower enantioselectivities were observed. The chiral silane was also shown to be synthetically useful for the construction of vicinal and remote chiral centers upon reaction with organometallic reagents.