905810-05-1Relevant academic research and scientific papers
Tertiary enamide-promoted diastereoselective domino: N-acyliminium ion trapping and nazarov cyclization
Zheng, Yongxiang,Andna, Lucile,Bistri, Olivia,Miesch, Laurence
, p. 6771 - 6775 (2020)
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.
