DOI QR코드

DOI QR Code

Direct Organocatalytic Regioselective α-Hydroxyamination of α-Branched Aldehydes

  • Kim, Sung-Gon (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Ahn, Eun-Ju (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Park, Tae-Ho (Medicinal Science Division, Korea Research Institute of Chemical Technology)
  • Published : 2007.10.20

Abstract

A direct regioselective α-hydroxyamination of α-branched aldehydes with nitrosobenzene using cis-5-benzylproline as catalyst has been developed for the preparation of α-hydroxyamino aldehydes possessing a quaternary carbon center. Such compounds are versatile building blocks for the synthesis of quaternary α- amino acids, β-amino alcohols, and 1,2-diamines.

Keywords

References

  1. Weinreb, S. M. Acc. Chem. Res. 2003, 36, 59-65 https://doi.org/10.1021/ar0200403
  2. Kobayashi, J.; Morita, H. Alkaloids 2003, 60, 165-205
  3. Ramon, D. J.; Yus, M. Curr. Org. Chem. 2004, 8, 149-183 https://doi.org/10.2174/1385272043486025
  4. Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 5127-5143
  5. Formaggio, F.; Pantano, M.; Crisma, M.; Toniolo, C.; Boesten, W. H. J.; Schoemaker, H. E.; Kamphuis, J.; Becker, E. L. Bioorg. Med. Chem. Lett. 1993, 3, 953-956 https://doi.org/10.1016/S0960-894X(00)80699-X
  6. Mossel, E.; Formaggio, F.; Crisma, M.; Toniolo, C.; Brexterman, Q. B.; Boestern, W. H. J.; Kamphuis, J.; Quaedflieg, P. J. L. M.; Temussi, P. Tetrahedron: Asymmetry 1997, 8, 1305-1314 https://doi.org/10.1016/S0957-4166(97)00127-4
  7. Bellier, B.; McCort- Tranchepain, I.; Ducos, B.; Danascimento, S.; Meudal, H.; Nobel, F.; Garbay, C.; Roques, B. P. J. Med. Chem. 1997, 40, 3947-3956 https://doi.org/10.1021/jm970439a
  8. Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382 https://doi.org/10.1021/bi00271a022
  9. Shirlin, D.; Gerhart, F.; Hornsperger, J. M.; Harmon, M.; Wagner, I.; Jung, M. J. Med. Chem. 1988, 31, 30-36 https://doi.org/10.1021/jm00396a007
  10. Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125. https://doi.org/10.1021/jo981297a
  11. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379-7388 https://doi.org/10.1021/ja00133a011
  12. Wenglowsky, S.; Hegedus, L. S. J. Am. Chem. Soc. 1998, 120, 12468-12473 https://doi.org/10.1021/ja9823518
  13. Park, K. H.; Kurth, M. J. Tetrahedron 1999, 55, 585-615 https://doi.org/10.1016/S0040-4020(98)00942-9
  14. Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 5127-5143
  15. Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569-623 https://doi.org/10.1016/j.tetasy.2007.02.003
  16. Kim, S.-G.; Park, T.-H. Tetrahedron Lett. 2006, 47, 9067-9071 https://doi.org/10.1016/j.tetlet.2006.10.081
  17. Guo, H.-M.; Cheng, L.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Chem. Commun. 2006, 429-431
  18. Kano, T.; Ueda, M.; Takai, J.; Maruoka, K. J. Am. Chem. Soc. 2006, 128, 6046- 6047 https://doi.org/10.1021/ja0604515
  19. Cheong, P. H.-Y.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 13912-13913 https://doi.org/10.1021/ja0464746
  20. Ezquerra, J.; Pedregal, C.; Rubio, A.; Valenciano, J.; Navio, J. L. G.; Alvarez-Builla, J.; Vaquero, J. J. Tetrahedron Lett. 1993, 39, 6317-6320
  21. van Esseveldt, B. C. J.; Vervoort, P. W. H.; van Delft, F. L.; Rutjes, F. P. J. T. J. Org. Chem. 2005, 70, 1791-1795 https://doi.org/10.1021/jo0484023
  22. Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011-5015 https://doi.org/10.1021/jo00121a020
  23. Cativiela, C. Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732 https://doi.org/10.1016/S0957-4166(99)00565-0
  24. Park, K. H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659 https://doi.org/10.1016/S0040-4020(02)00989-4

Cited by

  1. ChemInform Abstract: Direct Organocatalytic Regioselective α-Hydroxyamination of α-Branched Aldehydes. vol.39, pp.10, 2008, https://doi.org/10.1002/chin.200810053
  2. Synthesis of enantiomerically pure δ-benzylproline derivatives vol.39, pp.5, 2015, https://doi.org/10.1039/C4NJ01894J
  3. An efficient synthesis of (+)-epi-cytoxazone via asymmetric organocatalysis vol.19, pp.13, 2007, https://doi.org/10.1016/j.tetasy.2008.06.021
  4. Organocatalytic Asymmetric Friedel-Crafts Alkylation to γ-Hydroxy α,β-Unsaturated Aldehyde vol.30, pp.11, 2007, https://doi.org/10.5012/bkcs.2009.30.11.2519
  5. Organocatalytic Asymmetric Friedel-Crafts Alkylation to γ-Hydroxy α,β-Unsaturated Aldehyde vol.30, pp.11, 2007, https://doi.org/10.5012/bkcs.2009.30.11.2519