Novel water-soluble bisphosphinite chiral ligands derived from α,α- and β,β-trehalose. Application to asymmetric hydrogenation of dehydroamino acids and their esters in water or an aqueous/organic biphasic medium

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5593-5598

  Yonehara, Koji ^a   Hashizume, Tomohiro ^a   Mori, Kenji ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ESTER; HYDROXYL GROUP; LIGAND; PHOSPHINE DERIVATIVE; TREHALOSE;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; HYDROGENATION;

EID: 0033597845     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990448m     Document Type: Article

References (49)

1. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; John Wiley: New York, 1992.
2. (a) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Catalysis; VCH: New York, 1998.
3. (b) Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; VCH: New York, 1996.
4. (c) Joó, F.; Kathó, A. J. Mol. Catal. A: Chem. 1997, 116, 3.
5. (d) Papadogianakis, G.; Sheldon, R. A. New J. Chem. 1996, 20, 175.
6. (e) Cornils, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1575.
7. (f) Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Catal. A: Chem. 1995, 104, 17.
8. (g) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
9. Kuntz, E. G. Chemtech 1987, 17, 570.
10. (a) Lensink, C.; Rijnberg, E.; de Vries, J. G. J. Mol. Catal. A: Chem. 1997, 116, 199.
11. (b) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645.
12. (c) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449.
13. (d) Wan, K. T.; Davis, M. E. Tetrahedron: Asymmetry, 1993, 4, 2461.
14. (e) Tóth, I.; Hanson, B. E. Organometallics, 1993, 12, 1506.
15. (f) Laghmari, M.; Sinou, D. J. Organomet. Chem. 1992, 438, 213.
16. (g) Lensink, C.; de Vries, J. G. Tetrahedron: Asymmetry 1992, 3, 235.
17. (h) Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste, P.; Sinou, D. J. Chem. Soc., Chem. Commun. 1991, 1684.
18. (i) Sinou, D.; Safi, M.; Claver, M.; Masdeu, A. J. Mol. Catal. 1991, 68, L9.
19. (j) Tóth, I.; Hanson, B. E.; Davis, M. E. Tetrahedron: Asymmetry 1990, 1, 913.
20. (k) Tóth, I.; Hanson, B. E.; Davis, M. E. J. Organomet. Chem. 1990, 396, 363.
21. (l) Tóth, I.; Hanson, B. E.; Davis, M. E. Catal. Lett. 1990, 5, 183.
22. (m) Amrani, Y.; Lecomte, L.; Sinou, D.; Bakos, J.; Tóth, I.; Hell, B. Organometallics 1989, 8, 542.
23. (n) Lecomte, L.; Sinou, D. J. Mol. Catal. 1989, 52, L21.
24. (o) Alario, F.; Amrani, Y.; Colleuille, Y.; Dang, T. P.; Jenck, J.; Morel, D.; Sinou, D. J. Chem. Soc., Chem. Commun. 1986, 202.
25. (p) Nagel, U.; Kinzel, E. Chem. Ber. 1986, 119, 1731.
26. (q) Amrani, Y.; Sinou, D. J. Mol. Catal. 1986, 36, 319.
27. (r) Benhazma, R.; Amrani, Y.; Sinou, D. J. Organomet. Chem. 1985, 288, C37.
28. (s) Amrani, Y.; Sinou, D. J. Mol. Catal. 1984, 24, 231.
29. Eckl, R. W.; Priermeier, T.; Herrmann, W. A. J. Organomet. Chem. 1997, 532, 243.
30. Bakos, J.; Orosz, Á.; Cserépi, S.; Tóth, I.; Sinou, D. J. Mol. Catal. A: Chem. 1997, 116, 85.
31. (a) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 269.
32. (b) Ellis, J. W.; Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. Inorg. Chem. 1992, 31, 3026.
33. (c) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096.
34. (d) Chatt, J.; Leigh, R. M.; Slade, R. M. J. Chem. Soc., Dalton Trans. 1973, 2021.
35. (e) Issleib, K.; Möbius, M. Chem. Ber. 1961, 94, 102.
36. (a) Ferrara, M. L.; Oranona, I.; Ruffo, F.; Funicello, M.; Panunzi, A. Organometallics 1998, 17, 3832.
37. (a) Beller, M.; Krauter, J. G. E.; Zpaf, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 772.
38. (b) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829.
39. (c) Mitchell, T. N.; Heesche-Wagner, K. J. Organomet. Chem. 1992, 436, 43.
40. (a) Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197.
41. (b) Oehme, G.; Paetzold, E.; Selke, R. J. Mol. Catal. 1992, 71, L1.
42. (c) Selke, R. J. Organomet. Chem. 1989, 370, 241.
43. Wallace, P. A.; Minnikin, D. E. Carbohydr. Res. 1994, 263, 43.
44. Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967.
45. Cook, S. J.; Khan, R.; Brown, J. M. J. Carbohydr. Chem. 1984, 3, 343.
46. Hudson, C. S.; Dale, J. K. J. Am. Chem. Soc. 1918, 40, 992.
47. Allen, P. Z. Methods Carbohydr. Chem. 1962, 1, 372.
48. (a) Konradsson, P. K.; Udodong, U. E.; Fraster-Reid, B. Tetrahedron Lett. 1990, 31, 4313.
49. (b) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.