Stereoselective hydrogénation of folie acid with immobilized optically active rhodium(I)/diphosphane catalysts

Chemische Berichte

Volumn 130, Issue 1, 1997, Pages 55-62

  Brunner, Henri ^a   Bublak, Petra ^a   Helget, Martina ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Diastereoselective hydrog nation; Diphosphane catalysts; Folie acid; HPLC analysis of 5 formyltetrahydrofolic acid derivatives; Immobilized optically active rhodium(I); Leucovorin

Indexed keywords

EID: 0010502106     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300109     Document Type: Article

References (65)

1. H. Brunner, L. Wacenhuber, J. Organomet. Chem., in press.
2. W. Friedrich, Vitamins, De Gruyter, Berlin, 1988.
3. R. L. Blakley in The Biochemistry of Folie Acid and Related Pteridines (Eds.: A. Neuberger, E. L. Tatuni), vol. 13, NorthHolland Publishing Company, Amsterdam, 1969.
4. G. H. Hitchings, Angew. Chem. 1989, 707, 903;
5. Angen: Chem. Int. Eel. Engl. 1989, 28, 879.
6. B. A. Chabner, M. Slavik, Chemother. Rep. 1975, 6, 1.
7. N. Jafle, S. Howell, Adv. Cancer Chemother. 1979, 7, 111.
8. U. Lönn, S. Lönn, Biochem. Biophys. Res. Commun. 1986, 138, 54.
9. F. M. Sirotnak, P. L. Chello, D. M. Moccio, R. L. Kisliuk, G. Combepine, Y. Gaumont, J. A. Montcomery, Biochent. Pharm. 1979, 28, 2993.
10. C. Temple, J. D. Rose, W. R. Laster, J. A. Montcomery, Cancer Treat. Rep. 1981,65, 1117.
11. Physician's Desk Reference, 38th Ed., Medical Economics Co., Oradell, NJ, 1984, p. 821 and 1078.
12. J. C. Fontecille-Camps, C. E. Bruge, C. Temple, J. D. Rose, J. A. Montgomery, R. L. Kisliuk, J. Am. Chem. Soc. 1979, 707, 6114.
13. D. B. Cosulich, J. M. Smith, H. P. Broquist, J. Am. Chem. Soc. 1952, 74, 4215.
14. R. P. Leary, Y. Gaumont, R. L. Kisliuk, Biochem. Biophys. Res. Commun. 1973, 50, 484.
15. G. K. Smith, P. A. Benkovic, S. J. Benkovic, Biochemistry 1981, 20, 4034.
16. J. A. Straw, J. M. Covey, D. Szapary, Cancer Res. 1981,41, 3936.
17. J. A. Straw, W. T. Wynn, D. Szapary, Cancer Res. 1984,44, 3114.
18. M. May, T. J. Barger, M. Lansford, J. M. Ravel, G. L. Sutherland, W. Shive, T. J. Bardos, J. Am. Chem. Soc. 1951, 73, 3067.
19. B. Roth, M. E. Hultquist, M. J. Fahrenbach, E. L. R. Stokstad, D. B. Cosulich, H. P. Broquist, R. P. Parker, J. M. Smith, J. Am. Chem. Soc. 1952, 74, 3247.
20. A. Bobst, M. Viscontini, Helv. Chim. Acta 1966, 49, 875.
21. C. Temple, R. D. Elliot, J. D. Rose, J. A. Montgomery, J. Med. Chem. 1979,22,731.
22. L. Rees, C. J. Sucklinc, H. C. S. Wood, J. Chem. Soc., Chem. Commun. 1987, 470.
23. C. K. Mathews, F. M. Huennekens, J. Biol. Chem. 1969, 235, 3304.
24. H. R. Mueller, M. Ulman, J. Conti, G. Muerdel, PCTInt. Appl. WO 88 08,844 1988;
25. Chem. Abstr. 1989, 777, P 102722q.
26. G. Vecchi, PCT Int. Appl WO 93 15,076 1993;
27. Chem. Abstr. 1993, 779, P 226424d.
28. J. Feeney, B. Birdsall, J. P. Albrand, G. C. K. Roberts, A. S. Burgen, P. A. Chariten, D. W. Young, Biochemistry 1981, 20, 1837.
29. P. A. Charlton, D. W. Young, J. Chem. Soc.. Chem. Commun. 1979, 734.
30. L. Rees, E. Valente, C. J. Suckling, H. C. S. Wood, Tetrahedron 1986,42, 117.
31. T. Uwajima, T. Oshiro, T. Eguchi, Y. Kuge, A. Horiguchi, A. Igarashi, K. Mochida, M. Iwakura, Biochem. Biopltys. Res. Commun. 1990, 777, 684.
32. T. Eguchi, T. Oshiro, Y. Kuge, K. Mochida, T. Uwajima, Eur. Pat. Appl. EP 350934 1990;
33. Chem. Abstr. 1990, 7/2, P 234008s.
34. P. H. Boyle, M. T. Kcating, J. Chem. Soc., Chem. Commun. 1974, 375.
35. The hydrogénation procedure of ref.[30] was repeated several times. Using the HPLC analysis described in the present paper, the diastereomeric excess turned out to be 2.6-5.6% de.
36. K. E. Koenig in Asymmetric Synthesis (Ed.: J. D. Morrison), vol. 5, Academic Press, Orlando, 1985, p. 71.
37. H. Brunner, W. Zettlmeier, Handbook of enantioselectire catalysis with transition metal compounds, VCH, Weinheim, 1993.
38. H. Brunner, C. Huber, Chem. Bcr. 1992, 125, 2085.
39. P. Bublak, Dissertation, University of Regensburg, 1994.
40. M. Helget, Dissertation, University of Regensburg, 1996.
41. R. J. Mullin, D. S. Dutch, Chemistry and Biology of Pteridines, De Gruyter, Berlin, 1989, p. 167.
42. K. E. Choi, R. L. Shilsky, Anal. Biochem. 1988, 765, 398.
43. I. W. Wainer, R. M. Stiffm, J. Chromatogr, 1988, 424, 158.
44. L. Silan, P. Jadaud, L. R. Whitfield, I. W. Wainer, J. Chromatogr. 1990, 532, 227.
45. (R)-(+)-1,2-Bis(diphenylphosphanyl)propane, M. D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 1978, 700, 5491.
46. (,S,S)-2,3-Bis(diphenylphosphanyl)bicyclo[2.2.1]hept-5-ene, H. Brunner, W. Pieronczyk, Angew. Chem. 1979, 97, 655;
47. Angen: Chem. Int. Ed. Engl. 1979, 18, 620.
48. J. Bakos, I. Toth, B. Heil, L. Marko, J. Organomet. Chem. 1985, 279, 23.
49. K. Achiwa, J. Am. Chem. Soc. 1976, 95, 8265.
50. H. B. Kagan, T.-P. Dane, J. Am. Chem. Soc. 1972, 94, 6429.
51. B. A. Murrer, J. M. Brown, P. A. Chaloner, P. D. Nicholson, D. Parker, Synthesis 1979, 350.
52. H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 57, 629.
53. H. Brunner, H. J. Lautenschlager, W. A. König, R. Krebber, Chem. Der. 1990, 123, 847.
54. C. Hatat, N. Kokel, A. Mortreux, F. Petit, Tetrahedron Lett. 1990,37,4139.
55. A. Roucoux, F. Acbosson, A. Mortreux, F. Petit, Tetrahedron: Asymmetry 1993, 4, 2279.
56. (2S,4S)-4-DiphenyIphosphanyl-2-diphenylphosphanylmethyl-pyrrolidine, ref.[44].
57. (25,4S)-4-Dicyclohexylphosphanyl-2-diphenyIphosphanyl-methyl-N-methyl-1- pyrrolidinecarboxamide, H. Takeda, S. Ho-sokawa, M. Aburatani, K. Achiwa, Synlett, 1991, 193.
58. (2S,4S)-1-tert-ButoxycarbonyI-4-dicyclohexylphosphanyl-2-di- phenylphosphanylmethylpyrrolidine, H. Takahashi, M. Hattori, M. Chiba, T. Morimoto, K. Achiwa, Tetrahedron Lett. 1986, 27, 4477.
59. W. P. Fehlhammer, W. A. Herrmann, K. Öfele, Metallorganische Koinplexverbindungen (Ed.: G. Brauer), Handbuch der präparativen anorganischen Chemie, Enke Verlac, Stuttgart, 1981, vol. III, p. 1799.
60. G. Giordano, R. H. Crabtree, Inorg. Synth. 1990, 19, 218.
61. E. W. Abel, M. A. Bennett, G. Wilkinson, J. Chem. Soc. 1959, 3178.
62. R. Cramer, J. Am. Chem. Soc. 1964, 86, 217.
63. W. P. Fehlhammer, W. A. Herrmann, K. Öfele, Metallorganische Komplexverbindungen in G. Brauer (Ed.), Handbuch der präparativen anorganischen Chemie, Enke Verlac, Stuttgart, 1981, vol. III, 1896.
64. J. Chatt, L. M. Venanzi, J. Chem. Soc. 1957, 4735.
65. J. Powell, B. L. Shaw, J. Chem, Soc. A 1968, 583.