1629211-39-7Relevant academic research and scientific papers
NBS/DBU-Promoted One-Pot Three-Component Cycloaddition of Malonic Acid Derivatives, Nitrosoarenes, and Alkenes: Synthesis of Isoxazolidines
Li, Xing,Zheng, Leijie,Gong, Xiaolei,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
, p. 1096 - 1107 (2021)
A general DBU-mediated one-pot three-component cycloaddition reaction of easily accessible malonic acid derivatives, nitrosoarenes, and alkenes has been successfully established with the aid of NBS to provide direct access to highly functionalized isoxazolidine derivatives with generally good to excellent yields, broad functional group tolerance, and excellent regio- and diastereo-selectivities under mild conditions. The mechanism study shows that the NBS-mediated formation of bromomalonic acid derivatives from malonic acid derivatives and DBU-promoted synthesis of nitrone intermediates via the reaction of bromomalonic acid derivatives with nitrosoarenes are key steps.
Stereospecific formal [3+2] dipolar cycloaddition of cyclopropanes with nitrosoarenes: An approach to isoxazolidines
Chakrabarty, Shyamal,Chatterjee, Indranil,Wibbeling, Birgit,Daniliuc, Constantin Gabriel,Studer, Armido
supporting information, p. 5964 - 5968 (2014/06/10)
The MgBr2-catalyzed formal [3+2] cycloaddition of donor-acceptor activated cyclopropanes with nitrosoarenes offers a novel approach to various structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity. Product isoxazolidines can be readily transformed into α-amino lactones by reductive or decarboxylative N-O cleavage and subsequent lactonisation, and the N-aryl bond cleavage is also possible under oxidative conditions. Stereospecific and regioselective: The MgBr 2-catalyzed formal [3+2] cycloaddition of donor-acceptor-activated cyclopropanes with nitrosoarenes offers a novel approach to structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity.
