Xu, Chao; Muir, Calum W.; Leach, Andrew G.; Kennedy, Alan R.; Watson, Allan J. B. published the article 《Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation》. Keywords: azaheterocycle vinyl aniline phosphoric acid chiral conjugate addition catalyst; ethylamine azaheteroaryl stereoselective preparation; Brønsted acids; asymmetric catalysis; heterocycles; organocatalysis; stereochemistry.They researched the compound: Methyl 6-bromonicotinate( cas:26218-78-0 ).Safety of Methyl 6-bromonicotinate. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:26218-78-0) here.
The direct enantioselective synthesis of chiral azaheteroaryl ethylamines from vinyl-substituted N-heterocycles and anilines is reported. A chiral phosphoric acid (CPA) catalyst promotes dearomatizing aza-Michael addition to give a prochiral exocyclic aryl enamine, which undergoes asym. protonation upon rearomatization. The reaction accommodates a broad range of N-heterocycles, nucleophiles, and substituents on the prochiral center, generating the products in high enantioselectivity. DFT studies support a facile nucleophilic addition based on catalyst-induced LUMO lowering, with site-selective, rate-limiting, intramol. asym. proton transfer from the ion-paired prochiral intermediate.
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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem