Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Efficient Synthesis of Optically Active 2-N-Boc (or Cbz)-amino-1-arylethanols as Key Intermediates for Synthesis of Chiral Drugs via Asymmetric Reduction

  • Published : 2004.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Crossley, R. In Chirality and the Biological Activity of Drugs;CRC Press: New York, 1995.
  2. Pamies, O.; Bäckvall, J. E. J. Org. Chem. 2001, 66, 4022-4025. https://doi.org/10.1021/jo015579d
  3. Foelsche, E.; Hickel, A.; Hönig, H.; Seufer-Wasserthal, P. J. Org. Chem. 1990, 55, 1749. https://doi.org/10.1021/jo00293a015
  4. Lutje Spelberg, J. H.; van Hylckama Vlieg, J. E. T.; Tang, L.;Janssen, D. B.; Kellogg, R. M. Organic Lett. 2001, 41.
  5. Kamal, A.; Arifuddin, M.; Rao, M. V. Tetrahedron: Asymmetry 1999, 10,4261. https://doi.org/10.1016/S0957-4166(99)00464-4
  6. Martínez, L. E.; Leighton, J. L.; Carsten, D. H.;Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. https://doi.org/10.1021/ja00126a048
  7. Megro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc. Chem. Commun. 1995,1021.
  8. Guy, A.; Doussot, J.; Ferroud, C.; Garreau, A.;Godefroy-Falguieres, A. Synthesis 1992, 821.
  9. Guy, A.; Dubuffet, T.; Doussot, J.; Godefroy-Falguieres, A. Synlett 1991,403.
  10. Watanabe, M.; Murata, K.; Ikariya, T. J. Org. Chem. 2002, 67, 1712. https://doi.org/10.1021/jo011076w
  11. Yadav, J. S.; Reddy, P. T.; Hashim, S. R. Synlett 2000, 1049.
  12. Reddy, M. A.; Bhanumathi, N.; Rao, K. R. J. Chem. Soc. Chem.Commun. 2001, 1974.
  13. Yadav, J. S.; Reddy, P. T.; Nanda, S.; Rao, A. B. Tetrahedron:Asymmetry 2001, 12, 63. https://doi.org/10.1016/S0957-4166(01)00020-9
  14. Ziegler, T.; Horsch, B.; Effenberger, F. Synthesis 1990, 575.
  15. Midland, M. M.; Lee, P. E. J. Org. Chem. 1985, 50, 3239. https://doi.org/10.1021/jo00217a054
  16. Jackson, W. R.; Jacobs, H. A.; Jayatilake, G. S.; Matthews,B. R.; Watson, K. G. Aust. J. Chem. 1990, 43, 2045. https://doi.org/10.1071/CH9902045
  17. Stork, G.; Worrall, W. S.; Pappas, J. J. J. Am. Chem. Soc. 1960, 82,4315. https://doi.org/10.1021/ja01501a048
  18. Cho, B. T.; Kang, S. K.; Shin, S. H. Tetrahedron: Asymmetry 2002, 13, 1209. https://doi.org/10.1016/S0957-4166(02)00322-1
  19. Cho, B. T.; Kang, S. K.; Yang, W. K. Bull. Korean Chem. Soc. 2002, 23, 1328. https://doi.org/10.5012/bkcs.2002.23.9.1328
  20. Shin, S. H.; Kang, S. K.; Cho, B. T. Bull. Korean Chem. Soc. 2003, 24, 1695. https://doi.org/10.5012/bkcs.2003.24.11.1695
  21. Izumi, T.; Fukaya, K. Bull. Chem. Soc. Jpn. 1993, 66, 1216. https://doi.org/10.1246/bcsj.66.1216
  22. Izumi, T.; Satou, K.; Ono, K. J. Chem. Tech. Biotechnol. 1996, 66,233. https://doi.org/10.1002/(SICI)1097-4660(199607)66:3<233::AID-JCTB486>3.0.CO;2-X
  23. Kawamoto, A. M.; Wills, M. J. Chem. Soc. Perkin Trans. 1 2001, 1916.
  24. Itsuno, S.; Ito, K. J. Org. Chem. 1984, 49, 555. https://doi.org/10.1021/jo00177a036
  25. Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc. Perkin Trans. 1 1985, 2039. https://doi.org/10.1039/p19850002039
  26. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc.1987, 109, 5551. https://doi.org/10.1021/ja00252a056
  27. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925. https://doi.org/10.1021/ja00259a075
  28. Cho, B. T. Aldrichimica Acta 2002, 35, 3
  29. Ramachandran, P. V.; Brown, H. C. inReductions in Organic Synthesis (ACS Symposium Series 641);Abdel-Magid, A. F., Ed.; American Chemical Society: Washington,DC, 1996; pp 884-897.
  30. Cho, B. T.; Choi, O. K Bull. Korean Chem. Soc. 2001, 22, 443.

Cited by

  1. Lipase B vol.6, pp.11, 2016, https://doi.org/10.1021/acscatal.6b02192
  2. Efficient Synthesis of Optically Active 2-N-Boc (or Cbz)-amino-1-arylethanols as Key Intermediates for Synthesis of Chiral Drugs via Asymmetric Reduction. vol.35, pp.44, 2004, https://doi.org/10.1002/chin.200444087
  3. Catalytic Asymmetric β-Peroxidation of Nitroalkenes vol.350, pp.13, 2008, https://doi.org/10.1002/adsc.200800387
  4. Application of Microwave Activation Techniques to the N-Alkenyl Protection of Lactams vol.27, pp.2, 2004, https://doi.org/10.5012/bkcs.2006.27.2.286
  5. A Mild and Highly Efficient Synthesis of ChiralN-Dichloroacetyl-4-ethyl-1,3-oxazolidines : A Mild and Highly Efficient Synthesis of ChiralN-Dichloroacetyl-4-ethyl-1,3-oxazolidines vol.49, pp.4, 2004, https://doi.org/10.1002/jhet.886