Atroposelective synthesis of axially chiral imidazo[1,2-<i>a</i>]pyridines via asymmetric multicomponent reaction.

ABSTRACT: Imidazo[1,2-a]pyridines are privileged heterocycles with diverse applications in medicinal chemistry; however, the catalytic asymmetric synthesis of these heterocyclic structures remains underexplored. Herein, we present an efficient and modular approach for the atroposelective synthesis of axially chiral imidazo[1,2-a]pyridines via an asymmetric multicomponent reaction. By utilizing a chiral phosphoric acid catalyst, the Groebke-Blackburn-Bienaymé reaction involving various 6-aryl-2-aminopyridines, aldehydes, and isocyanides gave access to a wide range of imidazo[1,2-a]pyridine atropoisomers with high to excellent yields and enantioselectivities. Extensive control experiments underscored the pivotal role of the remote hydrogen bonding donor on the substrates in achiev

SUBMITTER: Hong S 

PROVIDER: S-EPMC11616709 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature