Organic Letters

, том 23 , издание 23 , страницы 9112-9117

Enantioselective Synthesis of 2-Functionalized Tetrahydroquinolines through Biomimetic Reduction

Тип публикации: Journal Article

Дата публикации: 2021-11-12

American Chemical Society (ACS)

Organic Letters

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SJR: 1.007

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.1c03430

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PubMed ID: 34766774

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

Biomimetic asymmetric reduction of 2-functionalized quinolines has been successfully developed with the chiral and regenerable NAD(P)H model CYNAM in the presence of transfer catalyst simple achiral phosphoric acids, providing the chiral 2-functionalized tetrahydroquinolines with up to 99% ee. Using this methodology as a key step, a chiral and potent opioid analgesic containing a 1,2,3,4-tetrahydroquinoline motif was synthesized with high overall yield.

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Zhao Z. B. et al. Enantioselective Synthesis of 2-Functionalized Tetrahydroquinolines through Biomimetic Reduction // Organic Letters. 2021. Vol. 23. No. 23. pp. 9112-9117.

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Zhao Z. B., Wang J., Zhu Z. H., Chen M., Zhou Y. Enantioselective Synthesis of 2-Functionalized Tetrahydroquinolines through Biomimetic Reduction // Organic Letters. 2021. Vol. 23. No. 23. pp. 9112-9117.

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TY - JOUR

DO - 10.1021/acs.orglett.1c03430

UR - https://doi.org/10.1021/acs.orglett.1c03430

TI - Enantioselective Synthesis of 2-Functionalized Tetrahydroquinolines through Biomimetic Reduction

T2 - Organic Letters

AU - Zhao, Zi Biao

AU - Wang, Jie

AU - Zhu, Zhou Hao

AU - Chen, Muwang

AU - Zhou, Yonggui

PY - 2021

DA - 2021/11/12

PB - American Chemical Society (ACS)

SP - 9112-9117

IS - 23

VL - 23

PMID - 34766774

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2021_Zhao,

author = {Zi Biao Zhao and Jie Wang and Zhou Hao Zhu and Muwang Chen and Yonggui Zhou},

title = {Enantioselective Synthesis of 2-Functionalized Tetrahydroquinolines through Biomimetic Reduction},

journal = {Organic Letters},

year = {2021},

volume = {23},

publisher = {American Chemical Society (ACS)},

month = {nov},

url = {https://doi.org/10.1021/acs.orglett.1c03430},

number = {23},

pages = {9112--9117},

doi = {10.1021/acs.orglett.1c03430}

}

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Zhao, Zi Biao, et al. “Enantioselective Synthesis of 2-Functionalized Tetrahydroquinolines through Biomimetic Reduction.” Organic Letters, vol. 23, no. 23, Nov. 2021, pp. 9112-9117. https://doi.org/10.1021/acs.orglett.1c03430.

Издатель

American Chemical Society (ACS)

Журнал

Organic Letters

SCImago Q1

Tоп 10% SCImago

WOS Q1

БС1