Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization

[Image: see text] Stereoselective synthesis of C(4)-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 e...

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Autores principales: Jung, Sunhwa, Yoon, Seungri, Lee, Jae Kyun, Min, Sun-Joon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9476524/
https://www.ncbi.nlm.nih.gov/pubmed/36120044
http://dx.doi.org/10.1021/acsomega.2c04154
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author Jung, Sunhwa
Yoon, Seungri
Lee, Jae Kyun
Min, Sun-Joon
author_facet Jung, Sunhwa
Yoon, Seungri
Lee, Jae Kyun
Min, Sun-Joon
author_sort Jung, Sunhwa
collection PubMed
description [Image: see text] Stereoselective synthesis of C(4)-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.
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spelling pubmed-94765242022-09-16 Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization Jung, Sunhwa Yoon, Seungri Lee, Jae Kyun Min, Sun-Joon ACS Omega [Image: see text] Stereoselective synthesis of C(4)-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. American Chemical Society 2022-08-31 /pmc/articles/PMC9476524/ /pubmed/36120044 http://dx.doi.org/10.1021/acsomega.2c04154 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Jung, Sunhwa
Yoon, Seungri
Lee, Jae Kyun
Min, Sun-Joon
Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
title Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
title_full Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
title_fullStr Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
title_full_unstemmed Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
title_short Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
title_sort stereoselective synthesis of benzo[a]quinolizidines via aerobic ddq-catalyzed allylation and reductive cyclization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9476524/
https://www.ncbi.nlm.nih.gov/pubmed/36120044
http://dx.doi.org/10.1021/acsomega.2c04154
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