Org. Lett. [SOPhy]

Abstract :

N-Acyliminium ions generated from enamidyl vinyl ketones provided cyclopentenoid-fused diazepines diastereoselectively using BF3·Et2O in one pot through a domino N-acyliminium ion trapping/Nazarov reaction, simultaneously generating three new stereogenic centers. The particular structural design of the cross-conjugated dienone dictates the torquoselectivity observed in this polarized Nazarov reaction. Various N-bridgehead polycyclic scaffolds of putative pharmacological interest were obtained. Cyclic voltammetry was used to support the preferred reaction sequence within this domino reaction.

Graphical Abstract :

 

 

Reference :

Tertiary Enamide-Promoted Diastereoselective Domino: N-Acyliminium Ion Trapping and Nazarov Cyclization

Yongxiang Zheng, Lucile Andna, Olivia Bistri, and Laurence Miesch

Org. Lett. 2020 – DOI :10.1021/acs.orglett.0c02251

 

Contact chercheur :

Laurence Miesch, équipe SOPhy (https://sophy.chimie.unistra.fr), Institut de Chimie (UMR 7177).