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

ACS Omega. 2022 Aug 31;7(36):32562-32568. doi: 10.1021/acsomega.2c04154. eCollection 2022 Sep 13.

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.

PMID:36120044 | PMC:PMC9476524 | DOI:10.1021/acsomega.2c04154

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