Synthesis of the dibenzofuran-based diphosphine ligand BIFAP and its water-soluble derivative BIFAPS and their use in ruthenium-catalyzed asymmetric hydrogenation

Chemistry - A European Journal

Volumn 5, Issue 9, 1999, Pages 2472-2482

  Sollewijn Gelpke, Arjan E ^a   Kooijman, Huub ^b   Spek, Anthony L ^b   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Asymmetric synthesis; Atropisomerism; Dibenzofuran; Enantioselectivity; Hydrogenations; P ligands

Indexed keywords

ACETOACETIC ACID; CINNAMIC ACID DERIVATIVE; DIBENZOFURAN DERIVATIVE; LIGAND; METHANOL; PHOSPHINE DERIVATIVE; SOLVENT; SULFONIC ACID DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; HYDROGENATION; SOLUBILITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0000513598     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990903)5:9<2472::AID-CHEM2472>3.0.CO;2-V     Document Type: Article

References (83)

1. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori, J. Am. Chem. Soc. 1980, 102, 7932; A. Miyashita, H. Takaya, T. Souchi, R. Noyori, Tetrahedron 1984, 40, 1245.
2. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori, J. Am. Chem. Soc. 1980, 102, 7932; A. Miyashita, H. Takaya, T. Souchi, R. Noyori, Tetrahedron 1984, 40, 1245.
3. a) H. Kumobayashi, Recl. Trav. Chim. Pays-Bas, 1996, 115, 201;
4. b) S. Akutagawa, Appl. Catal. A 1995, 128, 171.
5. H. Takaya, S. Akutagawa, R. Noyori, Org. Synth. 1989, 67, 20.
6. H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629.
7. X. Zhang, K. Mashima, K. Koyano, N. Sayo, H. Kumobayashi, S. Akutagawa, H. Takaya, Tetrahedron Lett. 1991, 32, 7283.
8. A. Kojima, C. D. J. Boden, M. Shibasaki, Tetrahedron Lett. 1997, 38, 3459.
9. R. Schmidt, M. Cereghetti, B. Heiser, P. Schoenholzer, H.-J. Hansen, Helv. Chim. Acta 1988, 71, 897.
10. T. Chiba, A. Miyashita, H. Nohira, H. Takaya, Tetrahedron Lett. 1993, 34, 2351, and references therein.
11. J. Foricher, B. Heiser, R. Schmid (Hoffmann-La Roche). US Pat. 5,302,738, 1994; Chem. Abstr. 1993, 118, 147774w.
12. J. Foricher, B. Heiser, R. Schmid (Hoffmann-La Roche). US Pat. 5,302,738, 1994; Chem. Abstr. 1993, 118, 147774w.
13. R. Schmidt, E. A. Broger, M. Cereghetti, Y. Crameri, J. Foricher, M. Lalonde, R. K. Muller, M. Scalone, G. Schoettel, U. Zutter, Pure Appl. Chem. 1996, 68, 131.
14. R. Schmidt, J. Foricher, M. Cereghetti, P. Schonholzer, Helv. Chim. Acta 1991, 74, 370.
15. M. Murata, T. Morimoto, K. Achiwa, Synlett 1991, 827.
16. H. Jendralla, C. H. Li, E. Paulus, Tetrahedron: Asymmetry 1994, 5, 1297.
17. K-T. Wan, M. E. Davis, J. Chem. Soc. Chem. Commun. 1993, 1262.
18. T. Horiuchi, T. Ohta, M. Stephan, H. Takaya, Tetrahedron: Asymmetry 1994, 5, 325
19. H. Ding, J. Kang, B. E. Hanson, C. W. Kohlpaintner, J. Mol. Catal. A 1997, 124, 21.
20. D. Cai, J. F. Payack, D. R. Bender, D. L. Hughes, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 7180; see also Chem. Eng. News 1995, October 9, 74.
21. D. Cai, J. F. Payack, D. R. Bender, D. L. Hughes, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 7180; see also Chem. Eng. News 1995, October 9, 74.
22. C. Laue, G. Schroder, D. Arlt, R. Grosser (Bayer AG), EP 643,065, 1995; Chem. Abstr. 1995, 123, 112406.
23. C. Laue, G. Schroder, D. Arlt, R. Grosser (Bayer AG), EP 643,065, 1995; Chem. Abstr. 1995, 123, 112406.
24. T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, P. Antognazza, E. Cesarotti, J. Chem. Soc. Chem. Commun. 1995, 685.
25. T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, P. Antognaza, E. Cesarotti, F. Demartin, T. Pilati, J. Org. Chem. 1996, 61, 6244.
26. M. V. Sargent, F. M. Dean Furans and their Benzo Derivatives: (ii) Reactivity in Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, p. 643.
27. R. C. Elderfield, Heterocyclic Compounds, Vol. 2, Wiley, New York, 1961, p. 123.
28. T. Keumi, N. Tomioka, K. Hamanaka, H. Kakihara, M. Fukushima, T. Morita, H. Kitajima, J. Org. Chem. 1991, 56, 4671.
29. E. S. Hand, S. C. Johnson, D. C. Baker, J. Org. Chem. 1997, 62, 1348.
30. T. Keumi, M. Nakamura, M. Kitamura, N. Tomioka, H. Kitajima, J. Chem. Soc. Perkin Trans. 2 1985, 909.
31. M. W. Haenel, D. Jakubik, E. Rothenberger, G. Schroth, Chem. Ber. 1991, 124, 1705.
32. M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer, P. W. N. M. van Leeuwen, K. Goubitz, J. Fraanje, Organometallics 1995, 14, 3081.
33. E. M. Vogl, J. Bruckmann, C. Kruger, M. W. Haenel, J. Organomet. Chem. 1996, 520, 249.
34. M. Cereghetti, W. Arnold, E. A. Broger, A. Rageot, Tetrahedron Lett. 1996, 37, 5347.
35. S. Kanemasa, Y. Oderaotoshi, H. Yamamoto, J. Tanaka, E. Wada, J. Org. Chem. 1997, 62, 6454, and references therein.
36. A. E. Sollewijn Gelpke, J. Fraanje, K. Goubitz, H. Schenk, H. Hiemstra, Tetrahedron 1997, 53, 5899.
37. N. K. Roberts, S. B. Wild, J. Am. Chem. Soc. 1979, 101, 6254.
38. K. J. Brown, M. S. Berry, K. C. Waterman, D. Lingenfelter, J. R. Murdoch, J. Am. Chem. Soc. 1984, 106, 4717.
39. M. Kawashima, R. Hirata, Bull. Chem. Soc. Jpn. 1993, 66, 2002.
40. E. P. Kyba, G. W. Gokel, F. de Jong, K. Koga, L. R. Sousa, M. G. Siegel, L. Kaplan, G. Dotsevi, Y. Sogah, D. J. Cram, J. Org. Chem. 1977, 42, 4173.
41. S. Oi, K. Kawagoe, S. Miyano, Chem. Lett. 1993, 79.
42. I. W. Davies, P. J. Reider, Chem. Ind. (London) 1996, June 3, 412.
43. J. L. de Boer, A. J. M. Duisenberg, Acta Crystallogr. Sect. A 1984, 40, C-410.
44. A. L. Spek, J. Appl. Crystallogr. 1988, 21, 578.
45. G. M. Sheldrick, SHELXS86, Program for Crystal Structure Determination, University of Göttingen, Germany, 1986.
46. G. M. Sheldrick, SHELXS97, Program for Crystal Structure Determinution, University of Göttingen, Germany, 1997.
47. F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, E. Nishioka, K. Yanagi, K-I. Moriguchi, Organometallics 1993, 12, 4188.
48. T. Hayashi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 1984, 106, 158.
49. Y. Amrani, D. Sinou, J. Mol. Catal. 1984, 24, 231.
50. F. Alario, Y. Amrani, Y. Colleuille, D. P. Dang, K. Jenck, D. Morel, D. Sinou, J. Chem. Soc. Chem. Commun. 1986, 202.
51. L. Lecomte, D. Sinou, J. Bakos, I. Toth, B. Heil, J. Organomet. Chem. 1989, 370, 277.
52. W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524, and references therein.
53. W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524, and references therein.
54. K-t. Wan, M. E. Davis, Tetrahedron: Asymmetry 1993, 4, 2461.
55. a) K-t. Wan, M. E. Davis, J. Catal. 1994, 148, 1;
56. b) K-t. Wan, M. E. Davis, J. Catal. 1995, 152, 25.
57. B. Cornils, Angew. Chem. 1995, 107, 1709; Angew. Chem. Int. Ed. Engl. 1995, 34, 1575.
58. B. Cornils, Angew. Chem. 1995, 107, 1709; Angew. Chem. Int. Ed. Engl. 1995, 34, 1575.
59. J. Bakos, A. Orosz, B. Heil, M. Laghmari, P. Lhoste, D. Sinou, J. Chem. Soc. Chem. Commun. 1991, 1684.
60. C. Lensink, J. G. de Vries, Tetrahedron: Asymmetry 1992, 3, 235.
61. T. Ishizaki, H. Kumobayashi (Takasago), EP 544,455, 1993; Chem. Abstr. 1993, 119, 181016d.
62. T. Ishizaki, H. Kumobayashi (Takasago), EP 544,455, 1993; Chem. Abstr. 1993, 119, 181016d.
63. G. M. Sheldrick, SHELXL97, Program for Crystal Structure Refinement, University of Gottingen, Germany, 1997.
64. P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219.
65. Aqueous-Phase Organometallic Catalysis - Concept and Applications (Eds.: B. Cornils, W. A. Herrmann), WILEY-VCH, 1998, p. 432.
66. T. Ikariya, Y. Ishii, H. Kawano, A. Arai, M. Saburi, S. Yoshikawa, S. Akutagawa, J. Chem. Soc. Chem. Commun. 1985, 922.
67. P. van der Sluis, A. L. Spek, Acta Crystallogr. Sect. A 1990, 46, 194.
68. M. Kitamura, M. Tokunaga, T. Ohkuma, R. Noyori, Org. Synth. 1993, 71, 1.
69. Review: D. J. Ager, S. A. Laneman, Tetrahedron: Asymmetry 1997, 8, 3327.
70. K. Mashima, K. Kusano, T. Ohta, R. Noyori, H. Takaya, J. Chem. Soc. Chem. Commun. 1989, 1208.
71. D value of neat methyl (R)-(-)-3-hydroxybutyrate known in literature. [D. Seebach, M. Zuger, Helv. Chim. Acta 1982, 65, 495].
72. D of the neat product. Therefore, the optical rotation of the mixture of product and starting material was measured. The enantiomeric excess was determined hy dividing this value hy the optical rotation of a mixture of enantiopure methyl (R)-(-)-3-hydroxybutyrate and methyl acetoacetate in the same ratio.
73. H. D. Flack, Acta Crystallogr. Sect. A 1983, 39, 876.
74. International Tables for Crystallography, Volume C (A. J. C. Wilson) 1992, Kluwer Academic, Dordrecht (The Netherlands)
75. A. L. Spek. Acta Crystallogr. Sect. A 1990, 46, C-34.
76. S. A. King, L. DiMichelle, Catalysis of Organic Reactions Vol. 62 (Eds.: M. Scaros, M. Prunier), Dekker, New York, 1995, p. 157; S. A. King, A. S. Thompson, A. O. King, T. R. Verhoeven, J. Org. Chem. 1992, 57, 6689.
77. S. A. King, L. DiMichelle, Catalysis of Organic Reactions Vol. 62 (Eds.: M. Scaros, M. Prunier), Dekker, New York, 1995, p. 157; S. A. King, A. S. Thompson, A. O. King, T. R. Verhoeven, J. Org. Chem. 1992, 57, 6689.
78. A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475.
79. A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475.
80. K. Mashima, T. Hino, H. Takaya, Tetrahedron Lett. 1991, 32, 3101.
81. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.
82. A. E. Sollewijn Gelpke, J. J. N. Veerman, M. Schreuder Goedheijt, P. C. J. Kamer, P. W. N. M. van Leeuwen, H. Hiemstra, Tetrahedron 1999, 55, 6657.
83. A. I. Vogel, A Text-book of Practical Organic Chemistry; Longman, London, 1956, 3rd ed., p. 967.