155931-09-2Relevant articles and documents
Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole
Dai, Haican,Yu, Sisi,Cheng, Wanli,Xu, Ze-Feng,Li, Chuan-Ying
, p. 6417 - 6420 (2017)
A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of α-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.
Tertiary enamide-promoted diastereoselective domino: N-acyliminium ion trapping and nazarov cyclization
Zheng, Yongxiang,Andna, Lucile,Bistri, Olivia,Miesch, Laurence
supporting information, p. 6771 - 6775 (2020/09/15)
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.