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Synfacts 2005(0): 0040-0040  
DOI: 10.1055/s-2005-869934
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Protonation of Silyl Enolates Catalyzed by a Binap-AgF Complex

Contributor(s): Mark Lautens, Y. Eric Fang
A. Yanagisawa*, T. Touge, T. Arai
Chiba University, Japan
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Publikationsverlauf

Publikationsdatum:
20. Juli 2005 (online)

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Significance

A catalytic enantioselective protonation of trimethylsilyl enol ethers using AgF·binap under very mild conditions (CH2Cl2-MeOH, -20 °C to 0 °C) is reported. Generally good to excellent yields and ee’s were obtained. This method allows for preparation of enantiomerically enriched α-chiral ketones from racemic ketones by silyl enol ether formation followed by enantioselective protonation.