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Selective Reduction of C-C Double Bonds of 2-Vinylaziridnes: Preparation of Enationmerically Pure 2-Alkylaziridines

  • Lee, Baeck-Kyoung (Department of Chemistry, Sogang University) ;
  • Sung, Bong-June (Department of Chemistry, Sogang University) ;
  • Lee, Won-Koo (Department of Chemistry, Sogang University) ;
  • Yoon, Doo-Ha (Department of Chemistry and Protein Research Centre for Bio-Industry, Hankuk University of Foreign Studies) ;
  • Ha, Hyun-Joon (Department of Chemistry and Protein Research Centre for Bio-Industry, Hankuk University of Foreign Studies)
  • 발행 : 2009.12.20

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참고문헌

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  7. Unpublished results. Catalytic hydrogenation of 2-vinyl substituted aziridines provides a mixture of ring C-N bond reduction product and also side chain reduction product. The C(2)-N bond energy difference calculation, between N-methyl-2-ethylaziridine and N-methyl-2-vinylaziridine, was performed on a PC using Spartan'04 Quantum Mechanics Program (PC/X86). The optimization of the geometry of neutral molecules and radicals were preliminarily obtained by a PM3 semiempirical method. The energy minimizations were then performed using B3LYP functional. The 6-31+G*, 6-31G* and 6-311+G* were used for all C, H, O, N, S, Cl atoms. All geometry optimizations were performed without symmetry constraints to ensure that the resultant geometry is not a local minimum. The absolute energies of the calculated species were obtained without corrections for zero point vibrational energy. The homolytic bond dissociation energy (Ehomol(BD)) for all species investigated was calculated using the equation: (Ehomol (BD)) = [Eabs(radical1) = Eabs(radical2)] - Eab (neutral molecule). The calculation shows the C(2)-N bond energy of N-methyl-2-vinylaziridine is 14.9 kcal/mol less than that of the N-methyl-2-ethylaziridine
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피인용 문헌

  1. Application of Regio- and Stereoselective Functional Group Transformations of Chiral Aziridine-2-carboxylates vol.3, pp.10, 2014, https://doi.org/10.1002/ajoc.201402098
  2. Nucleophile-Dependent Regio- and Stereoselective Ring Opening of 1-Azoniabicyclo[3.1.0]hexane Tosylate vol.9, pp.4, 2014, https://doi.org/10.1002/asia.201301551
  3. One-pot multiple reactions: asymmetric synthesis of 2,6-cis-disubstituted piperidine alkaloids from chiral aziridine vol.14, pp.27, 2016, https://doi.org/10.1039/C6OB00806B
  4. ChemInform Abstract: Selective Reduction of C-C Double Bonds of 2-Vinylaziridines: Preparation of Enantiomerically Pure 2-Alkylaziridines. vol.41, pp.18, 2010, https://doi.org/10.1002/chin.201018093
  5. An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines vol.66, pp.40, 2010, https://doi.org/10.1016/j.tet.2010.07.027
  6. A simple and straightforward approach toward selective C=C bond reduction by hydrazine vol.90, pp.9, 2012, https://doi.org/10.1139/v2012-057