3376-23-6Relevant articles and documents
Regio- and stereoselective synthesis of novel isoxazolidine heterocycles by 1,3-dipolar cycloaddition between C-phenyl- N -methylnitrone and substituted alkenes. Experimental and DFT investigation of selectivity and mechanism
Hellel, Djamila,Chafaa, Fouad,Khorief Nacereddine, Abdelmalek,Djerourou, Abdelhafid,Vrancken, Emmanuel
, p. 30128 - 30141 (2017)
A series of isoxazolidine heterocycles was synthesized through the 1,3-dipolar cycloaddition (13DC) reaction of C-phenyl-N-methylnitrone with different substituted alkenes. The structures and stereochemistry of the cycloadducts were determined by spectroscopic methods. These 13DC reactions are characterized by complete regioselectivity and high stereoselectivity. The molecular mechanism, reactivity and selectivity of these 13DC reactions have been investigated by means of transition state theory and reactivity indices derived from conceptual DFT using DFT methods at the B3LYP/6-31G(d,p) level of theory. The obtained results indicate that these cycloaddition reactions take place through a one-step synchronous mechanism with a non-polar mechanism and high activation energies. The theoretical results are in agreement with the experimental findings.
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.
Cucurbit[7]uril as a catalytic nanoreactor for one-pot synthesis of isoxazolidines in water
Floresta, Giuseppe,Gentile, Davide,Mineo, Placido G.,Nicosia, Angelo,Patamia, Vincenzo,Rescifina, Antonio
supporting information, p. 1194 - 1203 (2020/02/22)
The main objective of supramolecular chemistry is to mimic the macrosystems present in nature, a goal that fits perfectly with the green chemistry guidelines. The aim of our work is to use the hydrophobic cavity of cucurbit[7]uril (CB[7]) to mimic nature