The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Stereodivergent Synthesis of Chromanones and Flavanones via Intramolecular Benzoin Reaction》. Authors are Wen, Genfa; Su, Yingpeng; Zhang, Guoxiang; Lin, Qiqiao; Zhu, Yujin; Zhang, Qianqian; Fang, Xinqiang.The article about the compound:(5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroboratecas:1214711-48-4,SMILESS:ClC1=C(N2N=C3[N+]([C@@]4([H])[C@@](CC5=C4C=CC=C5)([H])OC3)=C2)C(Cl)=CC(Cl)=C1.F[B-](F)(F)F).COA of Formula: C18H13BCl3F4N3O. Through the article, more information about this compound (cas:1214711-48-4) is conveyed.
The strategy of stereodivergent reactions on racemic mixtures (stereodivergent RRM) was employed for the first time in intramol. benzoin reactions and led to the rapid access of chromanones/flavanones with two consecutive stereocenters. The easily separable stereoisomers of the products were obtained with moderate to excellent enantioselectivities in a single step. Catechol type additives proved crucial in achieving the desired diastereo- and enantioselectivities.
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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider