Tandem Dearomatization/Enantioselective Allylic Alkylation of Pyridines.

ABSTRACT: Herein, we report a multistep one-pot reaction of substituted pyridines leading to N-protected tetrahydropyridines with outstanding enantioselectivity (up to 97% ee). An iridium(I)-catalyzed dearomative 1,2-hydrosilylation of pyridines enables the use of N-silyl enamines as a new type of nucleophile in a subsequent palladium-catalyzed asymmetric allylic alkylation. This telescoped process overcomes the intrinsic nucleophilic selectivity of pyridines to synthesize enantioenriched, C-3-substituted tetrahydropyridine products that have been otherwise challenging to access.

SUBMITTER: Greßies S 

PROVIDER: S-EPMC10251512 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature