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Highly enantioselective catalytic synthesis of chiral pyridines.

ABSTRACT: General methods to prepare chiral pyridine derivatives are greatly sought after due to their significance in medicinal chemistry. Here, we report highly enantioselective catalytic transformations of poorly reactive ?-substituted alkenyl pyridines to access a wide range of alkylated chiral pyridines. The simple methodology involves reactivity enhancement via Lewis acid (LA) activation, the use of readily available and highly reactive Grignard reagents, and a copper-chiral diphosphine ligand catalyst. Apart from allowing the introduction of different linear, branched, cyclic, and functionalised alkyl chains at the ?-position of alkenyl pyridines, the catalytic system also shows high functional group tolerance.

SUBMITTER: Jumde RP

PROVIDER: S-EPMC5727103 | biostudies-other | 2017 Dec

REPOSITORIES: biostudies-other

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Highly enantioselective catalytic synthesis of chiral pyridines.

Jumde Ravindra P RP Lanza Francesco F Pellegrini Tilde T Harutyunyan Syuzanna R SR

Nature communications 20171212 1

General methods to prepare chiral pyridine derivatives are greatly sought after due to their significance in medicinal chemistry. Here, we report highly enantioselective catalytic transformations of poorly reactive β-substituted alkenyl pyridines to access a wide range of alkylated chiral pyridines. The simple methodology involves reactivity enhancement via Lewis acid (LA) activation, the use of readily available and highly reactive Grignard reagents, and a copper-chiral diphosphine ligand catal ...[more]

PMID: 29233959

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