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Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

ABSTRACT: A sequential intramolecular-intermolecular enantioselective alkene difunctionalization reaction has been developed which is thought to proceed through Pd-catalyzed quinone methide formation. The synthesis of new chiral heterocyclic compounds with adjacent chiral centers is achieved in enantiomeric ratios up to 99:1 and diastereomeric ratios up to 10:1.

SUBMITTER: Jensen KH

PROVIDER: S-EPMC2792916 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

Jensen Katrina H KH Pathak Tejas P TP Zhang Yang Y Sigman Matthew S MS

Journal of the American Chemical Society 20091201 47

A sequential intramolecular-intermolecular enantioselective alkene difunctionalization reaction has been developed which is thought to proceed through Pd-catalyzed quinone methide formation. The synthesis of new chiral heterocyclic compounds with adjacent chiral centers is achieved in enantiomeric ratios up to 99:1 and diastereomeric ratios up to 10:1. ...[more]

PMID: 19902942

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