Open Access
ACS Omega, volume 7, issue 36, pages 32562-32568
Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
1
Publication type: Journal Article
Publication date: 2022-08-31
General Chemistry
General Chemical Engineering
Abstract
Stereoselective synthesis of C4-substituted benzo[a]quinolizidines via redox-controlled catalytic C-C-bond-forming reactions was carried out. Aerobic DDQ-catalyzed allylation of N-Cbz tetrahydroisoquinolines efficiently provided α-allylated products 5, which were transformed to enones 6 via cross-metathesis reactions using the second-generation Hoveyda-Grubbs catalyst. Palladium-catalyzed hydrogenation of 6 prompted alkene reduction, protecting group removal, and intramolecular reductive amination in one step to afford the desired benzo[a]quinolizidines 7 as single diastereomers.
Top-30
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Progress in Heterocyclic Chemistry
1 publication, 50%
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Russian Chemical Reviews
1 publication, 50%
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Elsevier
1 publication, 50%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 50%
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Jung S. et al. Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization // ACS Omega. 2022. Vol. 7. No. 36. pp. 32562-32568.
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Jung S., Yoon S., Lee J. K., Min S. Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization // ACS Omega. 2022. Vol. 7. No. 36. pp. 32562-32568.
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TY - JOUR
DO - 10.1021/acsomega.2c04154
UR - https://doi.org/10.1021/acsomega.2c04154
TI - Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
T2 - ACS Omega
AU - Jung, Sunhwa
AU - Yoon, Seungri
AU - Lee, Jae Kyun
AU - Min, Sun-Joon
PY - 2022
DA - 2022/08/31 00:00:00
PB - American Chemical Society (ACS)
SP - 32562-32568
IS - 36
VL - 7
SN - 2470-1343
SN - 2470-1343
ER -
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@article{2022_Jung,
author = {Sunhwa Jung and Seungri Yoon and Jae Kyun Lee and Sun-Joon Min},
title = {Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization},
journal = {ACS Omega},
year = {2022},
volume = {7},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acsomega.2c04154},
number = {36},
pages = {32562--32568},
doi = {10.1021/acsomega.2c04154}
}
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MLA
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Jung, Sunhwa, et al. “Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization.” ACS Omega, vol. 7, no. 36, Aug. 2022, pp. 32562-32568. https://doi.org/10.1021/acsomega.2c04154.