Conjugate Addition–Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis
Тип публикации: Journal Article
Дата публикации: 2018-04-10
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 5.491
CiteScore: 22
Impact factor: 16.6
ISSN: 00027863, 15205126
PubMed ID:
29634250
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
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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ГОСТ
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Yin Y. et al. Conjugate Addition–Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis // Journal of the American Chemical Society. 2018. Vol. 140. No. 19. pp. 6083-6087.
ГОСТ со всеми авторами (до 50)
Скопировать
Yin Y., Dai Y., Jia H., Li J., Bu L., Qiao B., Zhao X., Jiang Z. Conjugate Addition–Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis // Journal of the American Chemical Society. 2018. Vol. 140. No. 19. pp. 6083-6087.
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RIS
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TY - JOUR
DO - 10.1021/jacs.8b01575
UR - https://doi.org/10.1021/jacs.8b01575
TI - Conjugate Addition–Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis
T2 - Journal of the American Chemical Society
AU - Yin, Yanli
AU - Dai, Yating
AU - Jia, Hongshao
AU - Li, Jiangtao
AU - Bu, Liwei
AU - Qiao, Baokun
AU - Zhao, Xiaowei
AU - Jiang, Zhiyong
PY - 2018
DA - 2018/04/10
PB - American Chemical Society (ACS)
SP - 6083-6087
IS - 19
VL - 140
PMID - 29634250
SN - 0002-7863
SN - 1520-5126
ER -
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BibTex (до 50 авторов)
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@article{2018_Yin,
author = {Yanli Yin and Yating Dai and Hongshao Jia and Jiangtao Li and Liwei Bu and Baokun Qiao and Xiaowei Zhao and Zhiyong Jiang},
title = {Conjugate Addition–Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis},
journal = {Journal of the American Chemical Society},
year = {2018},
volume = {140},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/jacs.8b01575},
number = {19},
pages = {6083--6087},
doi = {10.1021/jacs.8b01575}
}
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MLA
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Yin, Yanli, et al. “Conjugate Addition–Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis.” Journal of the American Chemical Society, vol. 140, no. 19, Apr. 2018, pp. 6083-6087. https://doi.org/10.1021/jacs.8b01575.
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