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

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.

SUBMITTER: Taylor AM

PROVIDER: S-EPMC2782534 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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

Taylor Alexander M AM Altman Ryan A RA Buchwald Stephen L SL

Journal of the American Chemical Society 20090701 29

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. ...[more]

PMID: 19580273

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