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Synfacts 2006(9): 0916-0916  
DOI: 10.1055/s-2006-949262
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Enantioselective Addition of Silyl Ketene Acetals to Ketones

Contributor(s): Mark Lautens, Andrew Martins
K. Oisaki, D. Zhao, M. Kanai*, M. Shibasaki*
The University of Tokyo, Japan
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Using a CuF/TaniaPhos/PhBF3K catalyst system with added (EtO)3SiF, a variety of unsymmetrical ketones and silyl ketene acetals were transformed to the corresponding chiral 3° alcohol with high levels of enantio- and diastereo­selectivity. For β-substituted silyl ketene acetals, the diastereomeric ratio is independent of the E/Z ratio of the starting material; thus this is the first example of catalytic and enantioselective addition of silyl ketene acetals to ketones.