Diastereoselective Synthesis of N-(p-Tosylsulfonyl)-2-Phenylaziridine Over a Novel Magnetically Recyclable Cu(II) Catalyst Accompanied with the NInversion Assessment at DFT

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:

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.

Cite this article as:

Ghavami Monireh, Koohi Maryam, Ahmadi Aliakbar, Zandi Hassan and Kassaee Z. Mohammad, Diastereoselective Synthesis of N-(p-Tosylsulfonyl)-2-Phenylaziridine Over a Novel Magnetically Recyclable Cu(II) Catalyst Accompanied with the NInversion Assessment at DFT, Combinatorial Chemistry & High Throughput Screening 2014; 17 (9) . https://dx.doi.org/10.2174/1386207317666140818201510