Bulletin of the Korean Chemical Society

  • 제30권12호
  • /
  • Pages.3123-3126
  • /
  • 2009
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

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
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

키워드

참고문헌

  1. (a) Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599.(Please refer to the other references for details:no.13-no.18) https://doi.org/10.1002/anie.199405991
  2. Lee, W. K.; Ha, H.-J. Aldrichimica Acta 2003, 36, 57
  3. (a) Yun, J. M.; Sim, T. B.; Hahm, H. S.; Lee, W. K.; Ha, H.-J. J. Org. Chem. 2003, 68, 7675.(Please refer to the other references for details:no.19-no.22) https://doi.org/10.1021/jo034755a
  4. Han, S.-M.; Ma, S.-h.; Ha, H.-J.; Lee, W. K. Tetrahedron 2008, 64, 11110 https://doi.org/10.1016/j.tet.2008.09.068
  5. Lee, B. K.; Kim, M. S.; Hahm, H. S.; Kim, D. S.; Lee, W. K.; Ha, H.-J. Tetrahedron 2006, 62, 8393-8397 https://doi.org/10.1016/j.tet.2006.06.024
  6. (a) Hwang, G.-I.; Chung, J.-H.; Lee, W. K. Tetrahedron 1996, 52, 12111.(Please refer to the other references for details:no.23-no.27) https://doi.org/10.1021/jo961168z
  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 Unpublished results.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
  8. (a) Margathe, J.-F.; Shipman, M.; Smith, S. C. Org. Lett. 2005, 7, 4987-4990.(Please refer to the other references for details:no.28-no.31) https://doi.org/10.1021/ol051953a
  9. (a) Gang, Z.; Kainan, Z.; Janis, L. Tetrahedron Lett. 2008, 49, 6797-6799.(Please refer to the other references for details:no.32-no.35) https://doi.org/10.1016/j.tetlet.2008.09.056
  10. Acid labile
  11. (a) Michael, H. H.; George, A. O. Org. Lett. 2002, 4, 1771.(Please refer to the other references for details:no.37-no.39) https://doi.org/10.1021/ol025844x
  12. (a) Lim, Y.; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431.(Please refer to the other references for details:no.40) https://doi.org/10.1016/0040-4039(95)01814-X
  13. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: New York, 1996; Vol. 1A, p.1.
  14. (c) Osborn, H. M. I.; Sweeney, J. B.; Tetrahedron: Asymmetry 1997, 8, 1693. https://doi.org/10.1016/S0957-4166(97)00177-8
  15. (d) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. https://doi.org/10.1055/s-2000-7097
  16. (e) Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Chemistry III; Metz, P., Ed.; Springer: Berlin, 2001, p. 93-124.
  17. (f) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. https://doi.org/10.1039/b006015l
  18. (g) Hu, X. E. Tetrahedron 2004, 60, 2701 https://doi.org/10.1016/j.tet.2004.01.042
  19. (b) Jang, S.-Y.; Ha, Y. H.; Ko, S. W.; Lee, W.; Lee, J.; Kim, S.; Kim, Y. W.; Lee, W. K.; Ha, H.-J. Bioorg. Med. Chem. Lett. 2004, 14, 3881. https://doi.org/10.1016/j.bmcl.2004.05.066
  20. (c) Kim, M. S.; Kim, Y.-W.; Hahm, H. S.; Jang, J. W.; Lee, W. K.; Ha, H.-J. Chem. Commun. 2005, 3062. https://doi.org/10.1039/b503750f
  21. (d) Yoon, H. J.; Kim, Y.-W.; Lee, B. K.; Lee, W. K.; Kim Y.; Ha, H.-J. Chem. Commun. 2007, 79. https://doi.org/10.1039/b612740a
  22. (b) Kim, Y; Ha, H.-J.; Yun, S. Y.; Lee, W. K. Chem. Commun. 2008, 4363 https://doi.org/10.1039/b809124b
  23. (b) Choi, S.-K.; Lee, J.-S.; Kim, J.-H.; Lee, W. K. J. Org. Chem. 1997, 62, 743-745. https://doi.org/10.1021/jo961168z
  24. (c) Bae, J. H.; Shin, S.-H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041. https://doi.org/10.1016/S0040-4020(99)00538-4
  25. (d) Shin, S.-H.; Han, E. Y.; Park, C. S.; Lee, W. K.; Ha, H.-J. Tetrahedron: Asymmetry 2000, 11, 3283. https://doi.org/10.1016/S0957-4166(00)00319-0
  26. (e) Lee, K.-D.; Suh, J.-M.; Park, J.-H.; Ha, H.-J.; Choi, H. G.; Park, C. S.; Chang, J. W.; Lee, W. K.; Dong, Y.; Yun, H. Tetrahedron 2001, 57, 9655.
  27. (f) Park, C. S.; Kim, M. S.; Sim, T. B.; Pyun, D. K.; Lee, C. H.; Lee, W. K. J. Org. Chem. 2003, 68, 43 https://doi.org/10.1021/jo025545l
  28. (b) Bussolo, V. D.; Romano, M. R.; Favero, L.; Pineschi, M.; Crotti, P. J. Org. Chem. 2006, 71, 1696-1699. https://doi.org/10.1021/jo051877p
  29. (c) Mita, T.; Fukuda, N.; Roca, F. X. ; Kanai, M.; Shibasaki, M. Org. Lett. 2007, 9, 259-262. https://doi.org/10.1021/ol062663c
  30. (d) Hman, J.; Jarevng, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148-8159. https://doi.org/10.1021/jo9612638
  31. (e) Ling, R.; Yoshida, M.; Mariano, P. S. J. Org. Chem. 1996, 61, 4439-4449 https://doi.org/10.1021/jo960316i
  32. (b) Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837. https://doi.org/10.1021/ja037450m
  33. (c) Trost, B. M.; Dong, G. Org. Lett. 2007, 9, 2357-2359. https://doi.org/10.1021/ol070742y
  34. (d) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. https://doi.org/10.1021/jo000608q
  35. (e) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. https://doi.org/10.1021/jo961760o
  36. (f) Iska, V. B. R.; Gais, H.-J.; Tiwari, S. K.; Babu, G. S.; Adrien, A. Tetrahedron Lett. 2007, 48, 7102-7107 https://doi.org/10.1016/j.tetlet.2007.07.216
  37. (b) Cusack, N. J.; Reese, C. B.; Risius, A. C.; Roozpeikar, B. Tetrahedron 1976, 32, 2157. https://doi.org/10.1016/0040-4020(76)85128-9
  38. (c) Hunig, S.; Muller, H. R.; Their, W. Angew. Chem. Intl. Ed. Engl. 1965, 4, 271. https://doi.org/10.1002/anie.196502711
  39. (d) Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507 https://doi.org/10.1021/jo9710137
  40. (b) Chang, J.-W.; Bae, J. H.; Shin, S.-H.; Park, C. S.; Choi, D.; Lee, W. K. Tetrahedron Lett. 1998, 39, 9193 https://doi.org/10.1016/S0040-4039(98)02095-4

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