3 years ago

Chiral Phosphoric Acid-Catalyzed Kinetic Resolution via Amide Bond Formation

Chiral Phosphoric Acid-Catalyzed Kinetic Resolution via Amide Bond Formation
Hisashi Yamamoto, Yasushi Shimoda
We describe the kinetic resolution of a readily available 2-pyridyl ester via an amide bond formation catalyzed by a chiral Brønsted acid. A chiral phosphoric acid bearing a 2,4,6-trimethyl-3,5-dinitrophenyl group at the 3,3′-position enabled this transformation with high selectivities. We also found that the addition of Lewis acid increased both the reactivity and selectivity in the substrate with a methoxy group.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b03592

DOI: 10.1021/jacs.7b03592

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