Enantioselective Synthesis of N-Benzylic Heterocycles: a Nickel- and Photoredox-Dual Catalysis Approach

C. Pezzetta, D. Bonifazi, R. W. M. Davidson.
Org. Lett. 2019, 21 (22), 8957-8961.
DOI: 10.1021/acs.orglett.9b03338


Reported herein is a dual nickel- and photoredox-catalysed modular approach for the preparation of enantioenriched N-benzylic heterocycles. α-Heterocyclic carboxylic acids, easily obtainable from common commercial material, are reported as suitable substrates for a decarboxylative strategy in conjunction with a chiral pyridine-oxazoline (PyOx) ligand, providing quick access to enantioenriched drug-like products. The presence of a directing group on the heterocyclic moiety is shown to be beneficial, affording improved stereoselectivity in a number of cases.

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