1.
ACS Omega
; 7(36): 32562-32568, 2022 Sep 13.
Artigo
em Inglês
| MEDLINE
| ID: mdl-36120044
RESUMO
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.