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Conjugate Addition–Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis
Abstract
An enantioselective protonation strategy has been successfully applied to the synthesis of chiral α-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 α-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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Cited by
Direct decarboxylative Giese reactions
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Metadata
- Authors
- Yin, Y., Dai, Y., Jia, H., Li, J., Bu, L., Qiao, B., Zhao, X., & Jiang, Z.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2018-04-10
- Volume
- 140
- Issue
- 19
- Pages
- 6083-6087
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2797421292
- Cited by
- 312
- References
- 30
- FWCI
- 13.19
- Type
- journal article
- Language
- en
- Open access
- closed
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