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

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2022 Sep 19

PMID 36120044

Authors

Sunhwa Jung

Seungri Yoon

Jae Kyun Lee

Sun-Joon Min

Affiliations

Soon will be listed here.

Abstract

Stereoselective synthesis of C-substituted benzo[]quinolizidines via redox-controlled catalytic C-C-bond-forming reactions was carried out. Aerobic DDQ-catalyzed allylation of -Cbz tetrahydroisoquinolines efficiently provided α-allylated products , which were transformed to enones via cross-metathesis reactions using the second-generation Hoveyda-Grubbs catalyst. Palladium-catalyzed hydrogenation of prompted alkene reduction, protecting group removal, and intramolecular reductive amination in one step to afford the desired benzo[]quinolizidines as single diastereomers.

Citing Articles

DDQ-catalyzed oxidative α-allylation of isochromans under aerobic conditions.

Lee S, Jung S, Hyeon S, Kim K, Min S RSC Adv. 2024; 14(53):39645-39652.

PMID: 39691218 PMC: 11650363. DOI: 10.1039/d4ra07586b.

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