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

Author(s): Monireh Ghavami, Maryam Koohi, Aliakbar Ahmadi, Hassan Zandi, Mohammad Z. Kassaee

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

Volume 17 , Issue 9 , 2014

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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.

Keywords: A. Nano Fe3O4, C. DFT, A. Copper(II), D. Diastereoselective.

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Article Details

VOLUME: 17
ISSUE: 9
Year: 2014
Published on: 07 November, 2014
Page: [756 - 762]
Pages: 7
DOI: 10.2174/1386207317666140818201510
Price: $65

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