66646-88-6Relevant articles and documents
A powerful azomethine ylide route mediated by TiO2photocatalysis for the preparation of polysubstituted imidazolidines
Liu, Anan,Ma, Dongge,Qian, Yuhang,Li, Jundan,Zhai, Shan,Wang, Yi,Chen, Chuncheng
, p. 2192 - 2197 (2021)
Lewis- and Br?nsted-acid catalyzed 1,3-dipolar cycloaddition between azomethine ylides and unsaturated compounds is an important strategy to construct five-membered N-heterocycles. However, such a catalytic route usually demands substrates with an electron-withdrawing group (EWG) to facilitate the reactivity. Herein, we report a TiO2photocatalysis strategy that can conveniently prepare five-membered N-heterocyclic imidazolidines from a common imine (N-benzylidenebenzylamine) and alcohols along the route of 1,3-dipolaron azomethine ylide but without pre-installed EWG substituents on the substrates. Our EPR results uncovered the previously unknown mutual interdependence between an azomethine ylide and TiO2photo-induced hvb+/ecb?pair. This transformation exhibited a broad scope with 21 successful examples and could be scaled up to the gram level.
Highly diastereoselective multicomponent synthesis of unsymmetrical imidazolines.
Peddibhotla, Satymaheshwar,Jayakumar,Tepe, Jetze J
, p. 3533 - 3535 (2002)
We report here a highly diastereoselective multicomponent synthesis of imidazolines. These low molecular weight scaffolds contain a four-point diversity applicable to alkyl, aryl, acyl, and hetereocyclic substitutions. [structure: see text]
Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo?-methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles
Gan, Zhenjie,Li, Ke,Zhang, Hui,Li, Er-Qing
supporting information, p. 1331 - 1340 (2020/11/30)
A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo?-addition?-of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- A nd enantioselectivity, broad substrate scope and mild reaction conditions.
Tunable Synthesis of α-Amino Boronic Esters from Available Aldehydes and Amines through Sequential One-Pot Dehydration and Copper-Catalyzed Borylacylation
Xia, Qi,Chang, Hua-Rong,Li, Juan,Wang, Jia-Yi,Peng, Yan-Qing,Song, Gong-Hua
, p. 2716 - 2724 (2020/01/31)
Copper-catalyzed multicomponent borylacylation of imines with acid chlorides and bis(pinacolato)diboron was developed for the preparation of synthetically useful and pharmacologically relevant α-amino boronic acid derivatives. Starting from a range of acid chlorides and imines with aryl, heteroaryl, and alkyl substituents, most of these ligand-free reactions proceeded smoothly at room temperature in moderate to good yields. Furthermore, a facile and convenient one-pot, multistep access to the direct synthesis of α-amino boronic acid derivatives from available aldehydes and amines was also developed.