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Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode


  • We thank Phil Jeffrey for X-ray crystallographic structure determination of 2 b and 3. Financial support provided by Princeton University and Boehringer Ingelheim is gratefully acknowledged. A.G.D. is an Alfred P. Sloan Foundation Fellow, an Eli Lilly Grantee, an Amgen Young Investigator, and a Roche Early Excellence in Chemistry Awardee.


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A nickel for your thoughts … An enantioselective nickel-catalyzed cross-coupling between N-acylpyridinium salts and organozinc reagents is reported. The catalytic system, which is comprised of an air-stable NiII source and a chiral phosphoramidite ligand, affords 2-substituted-2,3-dihydro-4-pyridones with up to >99 % ee.