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Synfacts 2007(5): 0504-0504  
DOI: 10.1055/s-2007-968453
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Pd-Catalyzed Allylation of Fluorinated Silyl Enol Ethers

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
É. Bélanger, K. Cantin, O. Messe, M. Tremblay, J.-F. Paquin*
Université Laval, Québec, Canada
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

The authors describe a nice method for the preparation of chiral quaternary carbon stereocenters containing a fluorine atom. Silyl enol ether substrates reacted under palladium catalysis with allylic carbonates; the allylation products are obtained with high ee (>90% in most cases). The t-Bu-PHOX ligand (1) provided the highest selectivities.