16089-73-9Relevant academic research and scientific papers
A highly diastereoselective [3+3] annulation reaction of aza-oxyallyl cations and nitrones
Chen, Rongxing,Sun, Shaofa,Wang, Gangqiang,Guo, Haibin
, p. 1916 - 1920 (2018)
An efficient synthesis of 1,2,4-oxadiazinan-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallyl cations with nitrones has been developed. The protocol features easy operation, excellent yields, excellent diastereo-control, broad substrate sco
Regio- and Enantioselective (3+3) Cycloaddition of Nitrones with 2-Indolylmethanols Enabled by Cooperative Organocatalysis
Li, Tian-Zhen,Liu, Si-Jia,Sun, Yu-Wen,Deng, Shuang,Tan, Wei,Jiao, Yinchun,Zhang, Yu-Chen,Shi, Feng
supporting information, p. 2355 - 2363 (2020/12/09)
The regio- and enantioselective (3+3) cycloaddition of nitrones with 2-indolylmethanols was accomplished by the cooperative catalysis of hexafluoroisopropanol (HFIP) and chiral phosphoric acid (CPA). Using this approach, a series of indole-fused six-membered heterocycles were synthesized in high yields (up to 98 %), with excellent enantioselectivities (up to 96 % ee) and exclusive regiospecificity. This approach enabled not only the first organocatalytic asymmetric (3+3) cycloaddition of nitrones but also the first C3-nucleophilic asymmetric (3+3) cycloaddition of 2-indolylmethanols. More importantly, theoretical calculations elucidated the role of the cocatalyst HFIP in helping CPA control the reactivity and enantioselectivity of the reaction, demonstrating a new mode of cooperative catalysis.
Synthesis of 1,2,4-oxadiazolidines via [3+2] cycloaddition of nitrones with carbodiimides
Chen, Yuan,Fuyue, Liuting,Wang, Gangqiang,Wang, Hang,Lu, Chun,Guo, Haibing,St. Amant, Chiara,Sun, Shaofa,Xing, Yalan
supporting information, p. 4329 - 4332 (2019/03/19)
An efficient [3+2] cycloaddition of nitrones and carbodiimides has been developed. This 1,3-dipolar cycloaddition features high regioselectivity, mild and metal-free conditions, excellent functional group compatibility, and a broad substrate scope. The X-ray structures of two regio-isomers confirmed the regioselectivity of this transformation.
1,3-Dipolar cycloadditions. Part-XV: Systematic spectroscopic investigations of C-aryl-N-methylnitrones
Banerji, Avijit,Acharjee, Nivedita,Biswas, Pizush Kanti
scheme or table, p. 63 - 67 (2010/05/02)
Several C-aryl-N-methylnitrones have been synthesised during the course of our work on 1,3-dipolar cycloadditions. Detailed systematic spectroscopic investigations of all these nitrones have been undertaken. These are reported along with some generalisati
1,3-Dipolar cycloadditions: Part VIII1-Microwave irradiation assisted synthesis of N-methyl-C-aryl nitrones
Banerji, Avijit,Biswas, Pizush Kanti,Sengupta, Piyali,Dasgupta, Saugandha,Gupta, Maya
, p. 880 - 881 (2007/10/03)
N-Methyl-C-arylnitrones have been synthesized in very high yields within a few minutes from N-methyl-hydroxylamine hydrochloride and aryl aldehydes in presence of sodium hydrogen carbonate in methylene chloride using the microwave irradiation technique.
Synthesis of functionalized sulfonamides via 1,3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate
Caddick, Stephen,Bush, Hannah D.
, p. 2489 - 2492 (2007/10/03)
(Matrix presented) An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectiv
