Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 19, Pages 6083-6087Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b01575
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Funding
- NSFC [21672052]
- Provincial Innovation Scientists and Technicians Troop Construction Projects
- Henen Provincial Science and Technology Department Natural Science Project [162300410002, 162102210193]
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An enantioselective protonation strategy has been successfully applied to the synthesis of chiral a-tertiary azaarenes. With a dual catalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is mediated by visible light, a variety of a-branched 2-vinylpyridines and 2-vinylquinolines with N-aryl glycines underwent a redox-neutral, radical conjugate addition-protonation process and provided valuable chiral 3-(2-pyridine/quinoline)-3-substituted amines in high yields with good to excellent enantioselectivities (up to >99% ee). An application of this methodology to a two-step synthesis of the enantiomerically pure medicinal compound pheniramine (Avil) is also presented.
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