Journal of the American Chemical Society 2009-07-29

Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Alexander M Taylor, Ryan A Altman, Stephen L Buchwald

Index: J. Am. Chem. Soc. 131(29) , 9900-1, (2009)

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Abstract

The enantioselective alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine ligand with both axial and phosphorus-based chirogenicity is reported. The resultant quaternary carbon stereocenters are formed in high enantiomeric excess, and the conditions tolerate a range of substitution on both the oxindole and the aryl/vinyl coupling partners.