Enantioselective hydrogenation in water catalysed by rhodium phosphine complexes bound to polyacrylic acid

Journal of Molecular Catalysis A: Chemical

Volumn 139, Issue 2-3, 1999, Pages 259-270

  Malmström, Torsten ^a   Andersson, Carlaxel ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

Biphasic; Enantioselective hydrogenation; Polyacrylic acid; Rhodium; Water soluble phosphines

Indexed keywords

PHOSPHINE DERIVATIVE; POLYACRYLIC ACID; POLYMER; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033525382     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(98)00178-2     Document Type: Article

References (67)

1. T. Malmström, C. Andersson, Chem. Comm. (1996) 1135.
2. P. Kalck, F. Monteil, Adv. Organomet. Chem. 34 (1992) 219.
3. W.A. Herrmann, C.W. Kohlpaintner, Angew. Chem. Int. Ed. Engl. 32 (1993) 1524.
4. F. Joo, A. Katho, J. Mol. Catal. A 116 (1997) 3.
5. J.P. Arhancet, M.E. Davis, J.S. Merola, B.E. Hanson, J. Catal. 121 (1990) 327.
6. G. Fremy, E. Monflier, J.-F. Carpentier, Y. Castanet, A. Mortreux, J. Catal. 162 (1996) 339.
7. H. Bahrmann, H. Bach, Phosphorus Sulfur 30 (1987) 611.
8. E.G. Kuntz, Chem. Tech. (1987) 570.
9. R.T. Smith, K. Ungon, L.J. Sanderson, M.C. Baird, Organometallics 2 (1983) 1138.
10. H. Dibowski, F.P. Schmidtchen, Tetrahedron 51 (1995) 2325.
11. J. Mannasen, Y. Dror, US Patent (1983) 4.415500.
12. A. Avey, D.M. Schut, T.J.R. Weakley, D.R. Tyler, Inorg. Chem. 32 (1993) 233.
13. S. Ahrland, J. Chatt, N.R. Davies, Q. Rev. 12 (1958) 265.
14. S. Ahrland, J. Chatt, N.R. Davies, A.A. Williams, J. Chem. Soc. (1958) 1403.
15. S. Ahrland, J. Chatt, N.R. Davies, A.A. Williams, J. Chem. Soc. 264 (1958) 276.
16. A.F. Borowski, D.J. Cole-Hamilton, G. Wilkinson, Nouv. J. Chem. 2 (1977) 137.
17. F. Joo, Z. Toth, M.T. Beck, Inorg. Chim. Acta 25 (1977) L61.
18. T. Bartik, B. Bartik, B.E. Hanson, T. Glass, W. Bebout, Inorg. Chem. 31 (1992) 2667.
19. W.A. Herrmann, J.A. Kulpe, W. Konkol, H. Bahrmann, J. Organomet. Chem. 389 (1990) 85.
20. W.A. Herrmann, J. Kellner, H. Riepl, J. Organomet. Chem. 389 (1990) 103.
21. C. Larpent, R. Dabard, H. Patin, Tetrahedron Lett. 28 (1990) 2507.
22. J.M. Grosselin, C. Mercier, G. Allmang, F. Grass, Organometallics 10 (1991) 2126.
23. E.G. Kuntz, Rhone-Poulenc Ind., 1976, Fr-B 2366237.
24. E.G. Kuntz, Rhone-Poulenc Ind., 1978, DE-B 2733516.
25. W.A. Herrmann, J.A. Kulpe, J. Kellner, H. Riepl, H. Bahrmann, W. Konkol, Angew. Chem. Int. Ed. Engl. 29 (1990) 391.
26. B. Cornils, E.G. Kuntz, J. Organomet. Chem. 177 (1995) 502.
27. H.B. Kagan, in: G. Wilkinson, F.G. Stone, E.N. Abel (Eds.), Comprehensive Organometallic Chemistry, Vol. 8, Pergamon, Oxford, 1982, p. 463.
28. J.D. Morrison, Asymmetric Synthesis, Ed Academic Press, New York, Vol. 5, 1985.
29. W.A. Nugent, T.V. RajanBabu, M.J. Burk, Science 259 (1993) 479.
30. W.S. Knowles, Acc. Chem. Res. 16 (1983) 106.
31. I. Ojima, N. Clos, C. Bastos, Tetrahedron 45 (1989) 6901.
32. H. Brunner, Angew. Chem. Int. Ed. Engl. 22 (1983) 897.
33. F. Agbossou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 95 (1995) 2485.
34. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori, J. Am. Chem. Soc. 102 (1980) 7932.
35. B.D. Vineyard, W.S. Knowles, M.J. Sabacky, G.L. Backman, D.J. Weinkauff, J. Am. Chem. Soc. 99 (1977) 5946.
36. H.B. Kagan, T.P. Dang, J. Am. Chem. Soc. 94 (1972) 6429.
37. M.D. Fryzuk, B.J. Bosnich, J. Am. Chem. Soc. 99 (1977) 6262.
38. H.T.T. Ohta, R. Noyori, in: I. Ojima (Ed.), Catalytic Asymmertic Synthesis, VCH Publishers, Weinheim, 1993, p. 1.
39. G. Parshall, W. Nugent, Chem. Tech. 18 (1988) 194.
40. Y. Amrani, D. Sinou, J. Mol. Catal. 24 (1984) 231.
41. Y. Amrani, L. Lecomte, D. Sinou, J. Bakos, I. Toth, B. Heil, Organometallics 8 (1989) 542.
42. I. Toth, B.E. Hanson, M.E. Davis, Tetrahedron Asymmetry 1 (1990) 913.
43. I. Toth, B.E. Hanson, M.E. Davis, Catal. Lett. 5 (1990) 183.
44. K. To-Wan, M.E. Davis, Tetrahedron Asymmetry 4 (1993) 2461.
45. L. Lecomte, D. Sinou, J. Bakos, I. Toth, B. Heil, J. Organomet. Chem. 370 (1989) 277.
46. T. Malmström, H. Weigl, C. Andersson, Organometallics 34 (1995) 2593.
47. K. Achiwa, J. Am. Chem. Soc. 98 (1976) 8265.
48. R. Uson, L.A. Oro, M.A. Gerralda, M.C. Claver, P. Lahuerta, Transit. Met. Chem. 4 (1979) 55.
49. Y.S. Klausner, M. Bodansky, Synthesis (1972) 453.
50. I. Ojima, T. Kogure, N. Yoda, J. Org. Chem. 45 (1980) 4728.
51. E. Renaud, M.C. Baird, J. Mol. Catal. 80 (1993) 43.
52. J. Halpern, D.P. Riley, A.S.C. Chan, J.J. Pluth, J. Am. Chem. Soc. 99 (1977) 8055.
53. C. Larpent, R. Dabard, H. Patin, New J. Chem. 12 (1988) 907.
54. G. Papadogianakis, J.A. Peters, L. Maat, R.A. Sheldon, J. Chem. Soc. Ser. Chem. Commun. (1995) 1105.
55. G. Oehme, E. Paetzold, R. Selke, J. Mol. Catal. 71 (1992) L1.
56. T. Malmström, C. Andersson, J. Mol. Catal. A 116 (1997) 237.
57. T. Malmström, C. Andersson, Poster, Fechem XII, Prague, 1-5 September, 1997.
58. N.N. Greenwood, A. Earnshaw, Chemistry of the Elements, Pergamon, 1984, p. 1068.
59. D.R. Rosseinsky, J. Chem. Soc. Dalton (1979) 731.
60. Z. Zhou, G. Facey, B.R. James, H. Alper, Organometallics 15 (1996) 2496.
61. M.P. Anderson, L.H. Pignolet, Inorg. Chem. 20 (1981) 4101.
62. D.F. Evans, H. Wennerström, The Colloidal Domain where Physics, Chemistry, Biology and Technology Meet. VCH Publishers, 1994, p. 295.
63. C.R. Landis, J. Halpern, J. Am. Chem. Soc. 109 (1987) 1746.
64. J. Halpern, in: J.D. Morrison (Ed.), Asymmetric Synthesis, Academic Press, New York, 1985, p. 41.
65. U. Nagel, B. Rieger, Organometallics 8 (1989) 1534.
66. D.P. Paterniti, P.J. Roman, J.D. Atwood, J. Chem. Soc. Ser. Chem. Commun. (1996) 2659.
67. D.P. Paterniti, P.J. Roman, J.D. Atwood, Organometallics 16 (1997) 3371.