Highly enantioselective catalytic synthesis of chiral pyridines

Ravindra P. Jumde, Francesco Lanza, Tilde Pellegrini and Syuzanna R. Harutyunyan ()
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Ravindra P. Jumde: University of Groningen
Francesco Lanza: University of Groningen
Tilde Pellegrini: University of Groningen
Syuzanna R. Harutyunyan: University of Groningen

Nature Communications, 2017, vol. 8, issue 1, 1-10

Abstract: 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 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 catalyst. Apart from allowing the introduction of different linear, branched, cyclic, and functionalised alkyl chains at the β-position of alkenyl pyridines, the catalytic system also shows high functional group tolerance.

Date: 2017
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DOI: 10.1038/s41467-017-01966-7

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