So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Zhang, Guoxiang; Yang, Shuang; Zhang, Xiaoyan; Lin, Qiqiao; Das, Deb. K.; Liu, Jian; Fang, Xinqiang researched 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 tetrafluoroborate( cas:1214711-48-4 ).Quality Control of (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 tetrafluoroborate.They published the article 《Dynamic Kinetic Resolution Enabled by Intramolecular Benzoin Reaction: Synthetic Applications and Mechanistic Insights》 about this compound( cas:1214711-48-4 ) in Journal of the American Chemical Society. Keywords: crystal mol structure enantioenriched tetralone; enantioenriched tetralone preparation dynamic kinetic resolution; heterocyclic carbene catalyzed intramol benzoin diketone mechanism; ketoester heterocyclic carbene catalyzed intramol benzoin mechanism. We’ll tell you more about this compound (cas:1214711-48-4).
The highly enantio-, diastereo-, and regioselective dynamic kinetic resolution of β-ketoesters and 1,3-diketones was achieved via a chiral N-heterocyclic carbene catalyzed intramol. cross-benzoin reaction. A variety of tetralone derivatives bearing two contiguous stereocenters and multiple functionalities were liberated in moderate to excellent yields and with high levels of stereoselectivity (>95% ee and >20:1 dr in most cases). In addition, the excellent regioselectivity control for aryl/alkyl 1,3-diketones, and the superior electronic differentiation of 1,3-diarylketones were highlighted. Moreover, a set of new mechanistic rationale that differs with the currently widely accepted understanding of intramol. benzoin reactions was established to demonstrate the superior preference of benzoin over aldol transformation. A coexistence of competitive aldol and benzoin reactions was detected, but a retro-aldol-irreversible benzoin process performs a vital role in the generation of predominant benzoin products. The most essential role of an N-electron-withdrawing substituent in triazolium catalysts was revealed to be accelerating the rate of the benzoin transformation, rather than suppressing the aldol process through reducing the inherent basicity of the catalyst.
There is still a lot of research devoted to this compound(SMILES：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)Quality Control of (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 tetrafluoroborate, and with the development of science, more effects of this compound(1214711-48-4) can be discovered.
Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider