932-33-2Relevant articles and documents
Transketolase Catalyzed Synthesis of N-Aryl Hydroxamic Acids
Fúster Fernández, Inés,Hecquet, Laurence,Fessner, Wolf-Dieter
, p. 612 - 621 (2021/12/08)
Hydroxamic acids are metal-chelating compounds that show important biological activity including anti-tumor effects. We have recently engineered the transketolase from Geobacillus stearothermopilus (TKgst) to convert benzaldehyde as a non-natur
Nitrosobenzene-Enabled Chiral Phosphoric Acid Catalyzed Enantioselective Construction of Atropisomeric N-Arylbenzimidazoles
An, Qian-Jin,Xia, Wang,Ding, Wei-Yi,Liu, Huan-Huan,Xiang, Shao-Hua,Wang, Yong-Bin,Zhong, Guofu,Tan, Bin
supporting information, p. 24888 - 24893 (2021/10/20)
Described herein is an imidazole ring formation strategy for the synthesis of axially chiral N-arylbenzimidazoles by means of chiral phosphoric acid catalysis. Two sets of conditions were developed to transform two classes of 2-naphthylamine derivatives into structurally diverse N-arylbenzimidazole atropisomers with excellent chemo- and regioselectivity as well as high levels of enantiocontrol. It is worth reflecting on the unique roles played by the nitroso group in this domino reaction. It functions as a linchpin by first offering an electrophilic site (N) for the initial C?N bond formation while the resulting amine performs the nucleophilic addition to form the second C?N bond. Additionally, it could facilitate the final oxidative aromatization as an oxidant. The atropisomeric products could be conveniently elaborated to a series of axially chiral derivatives, enabling the exploitation of N-arylbenzimidazoles for their potential utilities in asymmetric catalysis.
Enantioselective Oxidative Coupling of β-Ketocarbonyls and Anilines by Joint Chiral Primary Amine and Selenium Catalysis
Chen, Wanting,Wang, Yanni,Mi, Xueling,Luo, Sanzhong
supporting information, p. 8178 - 8182 (2019/10/16)
An enantioselective primary amine-catalyzed total N-selective nitroso aldol reaction (N-NA) was achieved through the oxidation of primary aromatic amines to the corresponding nitrosoarenes catalyzed by selenium reagents and 30% H2O2. This protocol provides a facile and highly efficient access to α-hydroxyamino carbonyls bearing chiral quaternary centers under exceedingly mild and green reaction conditions with high chemo-and enantiocontrol.