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Synfacts 2010(12): 1394-1394  
DOI: 10.1055/s-0030-1258883
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Allylic Alkylation with Phosphaalkene-Oxazoline Ligands

Contributor(s): Mark Lautens, Norman Nicolaus
J. Dugal-Tessier, G. R. Dake, D. P. Gates*
University of British Columbia, Vancouver, Canada
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

This work represents the first example of an enantioselective palladium-catalyzed process using a bidentate chiral P(sp²)-N(sp²)-phosphaalkene ligand. It has been shown that the complex 1 can be used to achieve good to reasonable enantioselectivities (40-92% ee) in the allylic alkylation of 1,3-diphenyl-2-propenyl acetate with various malonate nucleophiles. The best results could be achieved with a base system composed of BSA/AcOK and OTf- as the counterion.