Stereoselective, nonracemic synthesis of ω-borono-α-amino acids

Tetrahedron Asymmetry

Volumn 9, Issue 12, 1998, Pages 2121-2131

  Collet, Sylvain ^a   Bauchat, Patrick ^a   Danion Bougot, Renée ^a   Danion, Daniel ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; ALPHA AMINO ACID; BROMIDE; GLYCINE; NICKEL; SCHIFF BASE;

ARTICLE; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032546884     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00186-4     Document Type: Article

References (24)

1. Morin, C. Tetrahedron 1994, 50, 12521-12569.
2. Matteson, D. S. In Stereodirected Synthesis with Organoboranes; Springer-Verlag: Berlin, Heidelberg, 1995; pp. 196-202.
3. (a) Tian, Z.-Q.; Brown, B. B.; Mack, D. P.; Hutton, C. A.; Bartlett, P. A. J. Org. Chem. 1997, 62, 514-522 and references therein.
4. (b) Snow, R. J.; Bachovchin, W. W.; Barton, R. W.; Campbell, S. J.; Coutts, S. J.; Freeman, D. M.; Gutheil, W. G.; Kelly, T. A.; Kennedy, C. A.; Krolikowski, D. A.; Leonard, S. F.; Pargellis, C. A.; Tong, L.; Adams, J. J. Amer. Chem. Soc. 1994, 116, 10860-10869.
5. (c) Kettner, C. A.; Shenvi, A. B. J. Biol. Chem. 1984, 259, 15106-15114.
6. (d) Wityak, J.; Earl, R. A.; Abelman, M. M.; Bethel, Y. B.; Fisher, B. N.; Kauffman, G. S.; Kettner, C. A.; Ma, P.; McMillan, J. L.; Mersinger, L. J.; Pesti, J.; Pierce, M. E.; Rankin, F. W.; Chorvat, R. J.; Confalone, P. N. J. Org. Chem. 1995, 60, 3717-3722.
7. Excitatory Amino Acid Receptors, Design of Agonists and Antagonists; Krogsgaard-Larsen, P.; Hansen, J. J., Eds. Ellis Horwood: New York, London, 1992.
8. Kinder, D. H.; Ames, M. M. J. Org. Chem. 1987, 52, 2452-2454.
9. Kinder, D. H.; Frank, S. K.; Ames, M. M. J. Med. Chem. 1990, 33, 819-823.
10. Baggio, R.; Elbaum, D.; Kanyo, Z. F.; Carroll, P. J.; Cavalli, R. C.; Ash, D. E.; Christianson, D. W. J. Amer. Chem. Soc. 1997, 119, 8107-8108.
11. Denniel, V.; Bauchat, P.; Danion, D.; Danion-Bougot, R. Tetrahedron Lett. 1996, 37, 5111-5114.
12. Belokon, Y. N. Janssen Chimica Acta 1992, 10, 4-12.
13. Commercially available from ACROS Organics, catalog no. 27541-2500.
14. Leukart, O.; Caviezel, M.; Eberle, A.; Escher, E.; Tun-Kyi, A.; Schwyzer, R. Helv. Chim. Acta 1976, 59, 2181-2183.
15. Brown, H. C.; Jadhav, P. K.; Desai, M. C. J. Amer. Chem. Soc. 1982, 104, 4303-4304.
16. Höfle, G.; Steglish, W.; Daniel, H. Chem. Ber. 1976, 109, 2648-2650.
17. Belokon, Y. N.; Bulychev, A. G.; Vitt, S. V.; Struchkov, Y. T.; Batsanov, A. S.; Timofeeva, T. V.; Tsyryapkin, V. A.; Ryzhov, M. G.; Lysova, L. A.; Bakhmutov, V. I.; Belikov, V. M. J. Amer. Chem. Soc. 1985, 107, 4252-259.
18. Belokon, Y. N.; Chernoglazova, N. I.; Ivanova, E. V.; Popkov, A. N.; Saporovskaya, M. B.; Suvorov, N. N.; Belikov, V. M. Bull. Acad. Sci. URSS, Div. Chem. Sci. (Engl. transl.) 1988, 37, 2541-2544; Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2818-2821.
19. Belokon, Y. N.; Chernoglazova, N. I.; Ivanova, E. V.; Popkov, A. N.; Saporovskaya, M. B.; Suvorov, N. N.; Belikov, V. M. Bull. Acad. Sci. URSS, Div. Chem. Sci. (Engl. transl.) 1988, 37, 2541-2544; Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2818-2821.
20. Losilkina, V. I.; Sokolov, V. I. Dokl. Chem. (Engl. transl.) 1991, 320, 243-245; Dokl. Akad. Nauk SSSR, Ser. Khim. 1991, 320, 339-342.
21. Losilkina, V. I.; Sokolov, V. I. Dokl. Chem. (Engl. transl.) 1991, 320, 243-245; Dokl. Akad. Nauk SSSR, Ser. Khim. 1991, 320, 339-342.
22. Ohfune, Y.; Nishio, H. Tetrahedron Lett. 1984, 25, 4133-4136.
23. Fauchère, J. L.; Leukart, O.; Eberle, A.; Schwyzer, R. Helv. Chim. Acta 1979, 62, 1385-1395.
24. Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988; Chapter 5, p. 426.