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Nickel-catalyzed enantioselective arylation of pyridine.

ABSTRACT: We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridiniumions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.

SUBMITTER: Lutz JP

PROVIDER: S-EPMC5207490 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Nickel-catalyzed enantioselective arylation of pyridine.

Lutz J Patrick JP Chau Stephen T ST Doyle Abigail G AG

Chemical science 20160308 7

We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridiniumions formed <i>in situ</i> from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step. ...[more]

PMID: 28058106

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