Title:Diastereoselective Synthesis of N-(p-Tosylsulfonyl)-2-Phenylaziridine Over a Novel Magnetically Recyclable Cu(II) Catalyst Accompanied with the NInversion Assessment at DFT
VOLUME: 17 ISSUE: 9
Author(s):Monireh Ghavami, Maryam Koohi, Aliakbar Ahmadi, Hassan Zandi and Mohammad Z. Kassaee
Affiliation:Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.
Keywords:A. Nano Fe3O4, C. DFT, A. Copper(II), D. Diastereoselective.
Abstract:An experimental and theoretical study has been carried out on diastereoselective aziridation of styrene over a
magnetically recyclable copper(II) catalyst: Cu(acac)2/NH2-T/SiO2@Fe3O4NPs. The turnover number (TON) of our
heterogeneous catalyst appears considerably higher than that reported for the homogeneous Cu(acac)2. Successive
applications of solid Cu(acac)2/NH2-T/SiO2@Fe3O4NPs have a slight effect on its catalytic activity. Between anticipated
cis and trans diastereomeric products, formation of only one is suggested by NMR. Even though, the trans-invertomer
appears thermodynamically more stable at B3LYP/AUG-cc-pVTZ//B3LYP/6-31+G+G* level, we propose formation of the
kinetically more stable cis-invertomer due to π-stacking between the tosyl group and the phenyl of styrene. The possibility
of cis-trans conversion is ruled out by the high energy barrier of > 76.9 kcal/mol probed in toluene, CCl4, C7H16, DMSO,
CH3CN, and H2O.
