Enantioselective hydroformylation of olefins catalyzed by rhodium(I) complexes of chiral phosphine-phosphite ligands

Topics in Catalysis

Volumn 4, Issue 3-4, 1997, Pages 175-185

  Nozaki, Kyoko ^a   Takaya, Hidemasa ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Chiral phosphine phosphite ligands; Enantioselective hydroformylation; Rhodium(I) complexes

Indexed keywords

EID: 0000012141     PISSN: 10225528     EISSN: None     Source Type: Journal    
DOI: 10.1023/a:1019144423541     Document Type: Article

References (54)

1. Review articles for asymmetric hydroformylation: (a) F. Agbossou, J.-F. Carpentier and A. Mortreux, Chem. Rev. 95 (1995) 2485;
2. (b) S. Gladiali, J.C. Bayón and C. Claver, Tetrahedron: Asymmetry 6 (1995) 1453;
3. (c) G. Consiglio, in: Catalytic Asymmetric Synthesis, ed. I. Ojima (V.C.H. Publishers Inc., New York, 1993) p. 273;
4. (d) C. Botteghi, S. Paganelli, A. Schionato and M. Marchetti, Chirality 3 (1991) 355;
5. (e) J.K. Stille, in: Comprehensive Organic Synthesis, Vol. 4, eds. B.M. Trost, I. Fleming and M.F. Semmelhack (Pergamon Press, Oxford, 1991) p. 927;
6. (f) I. Ojima and K. Hirai, in: Asymmetric Synthesis, Vol. 5, ed. J.D. Morrison (Academic Press, Orlando, 1985) p. 126;
7. (g) G. Consiglio and P. Pino, Top. Current Chem. 105 (1982) 77;
8. (h) P. Pino, G. Consiglio, C. Botteghi and C. Salomon, Adv. Chem. Ser. 132 (1974) 295.
9. (a) G. Consiglio, S.C.A. Nefkens and A. Borer, Organometallics 10 (1991) 2046;
10. (b) J.K. Stille, H. Su, P. Brechot, G. Parrinello and L.S. Hegedus, Organometallics 10 (1991) 1183.
11. (a) C.F. Hobbs and W.S. Knowles, J. Org. Chem. 46 (1981) 4422;
12. (b) S. Gladiali and L. Pinna, Tetrahedron: Asymmetry 1 (1990) 693;
13. (c) G. Stanley, in: Catalysis of Organic Reactions, eds. M.G. Scaros and M.L. Prunier (Marcel Dekker, Inc., New York, 1995) p. 363.
14. (a) P.W.N.M. van Leeuwen and C.F. Roobeek (Shell Ltd.), EP 54986 (1982); Chem. Abstr.;
15. (b) P.W.N.M. van Leeuwen and C.F. Roobeek, Organomet. Chem. 258 (1983) 343;
16. (c) E. Billig, A.G. Abatjoglou and D.R. Bryant (Union Carbide Ltd.), US Pat. 4769498 (1988); Chem. Abstr.;
17. (d) G.D. Cuny and S.L. Buchwald, J. Am. Chem. Soc. 115 (1993) 2066;
18. (e) A. van Rooy, E.N. Orij, P.C.J. Kamer and P.W.N.M. van Leeuwen, Organometallics 14 (1995) 34.
19. (a) D.J. Wink, T.J. Kwok and A. Yee, Inorg. Chem. 29 (1990) 5006;
20. (b) J. Kwok and D. Wink, J. Organometallics 12 (1993) 1954;
21. (c) N. Sakai, K. Nozaki, K. Mashima and H. Takaya, Tetrahedron: Asymmetry 3 (1992) 583;
22. (d) G.J.H. Buisman, P.C.J. Kamer and P.W.N.M. van Leeuwen, Tetrahedron: Asymmetry 4 (1993) 1625;
23. (e) J.E. Babin and G.T. Whiteker (Union Carbide Ltd.), U.S. Pat. 911518 (1992);
24. (f) G.J.H. Buisman, M.E. Martin, E.J. Vos, A. Klootwijik, P.C.J. Kamer and P.W.N.M. van Leeuwen, Tetrahedron: Asymmetry 6 (1995) 719;
25. (g) G.J.H. Buisman, E.J. Vos, P.C.J. Kamer and P.W.N.M. van Leeuwen, J. Chem. Soc., Dalton Trans. (1995) 409.
26. (a) N. Sakai, K. Nozaki, S. Mano and H. Takaya, J. Am. Chem. Soc. 115 (1993) 7033;
27. (b) K. Nozaki, N. Sakai, S. Mano, T. Higashijima, T. Horiuchi and H. Takaya, J. Am. Chem. Soc. 119 (1997) 4413.
28. (a) L. Kurz, G. Lee, D. Morgans, Jr., M.J. Waldyke and T. Ward, Tetrahedron Lett. 31 (1990) 6321;
29. (b) Y. Uozumi, A. Tanahashi, S.-Y. Lee and T. Hayashi, J. Org. Chem. 58 (1993) 1945.
30. T. Higashijima, N. Sakai, K. Nozaki and H. Takaya, Tetrahedron Lett. 35 (1994) 2023.
31. J.-P. Rieu, A. Boucherle, H. Cousse and G. Mouzin, Tetrahedron 42 (1986) 4095.
32. N. Sakai, K. Nozaki and H. Takaya, J. Chem. Soc., Chem. Commun. (1994) 395.
33. K. Nozaki, T. Nanno and H. Takaya, J. Organomet. Chem. 527 (1997) 103.
34. C. Botteghi, M. Branka and A. Saba, J. Organomet. Chem. 184 (1980) C17.
35. (a) T. Horiuchi, T. Ohta, K. Nozaki and H. Takaya, Chem. Commun. (1996) 155;
36. (b) T. Horiuchi, T. Ohta, E. Shirakawa, K. Nozaki and H. Takaya, Tetrahedron 53 (1997) 7795.
37. Y Ikada, in: Polymers and Biomaterials, eds. H. Feng, Y Han and L. Huang (Elsevier Science Publishers, Amsterdam, 1991) p. 273, and references cited therein.
38. T. Nanno, N. Sakai, K. Nozaki and H. Takaya, Tetrahedron: Asymmetry 6 (1995) 2583.
39. J. Wildeman and A.M. van Leusen, Synthesis (1979) 733.
40. (a) I. Ojima, Chem. Rev. 68 (1988) 1011;
41. (b) I. Ojima, K. Kato, M. Okabe and T. Fuchikami, J. Am. Chem. Soc. 109 (1987) 7714.
42. S. Gladiali, G. Faedda, M. Marchetti and C. Botteghi, J. Organomet. Chem. 244 (1983) 289.
43. T. Horiuchi, T. Ohta, E. Shirakawa, K. Nozaki and H. Takaya, J. Org. Chem., in press.
44. (a) J.T. Sime, R.D. Barnes, S.W. Elson, R.L. Jarvset and K.J. O'Toole, J. Chem. Soc., Perkin Trans, l (1992) 1653;
45. (b) D.S. Larsen, A. Schofield, R.J. Stoodley and P.D. Tiffin, Tetrahedron Lett. 35 (1994) 9285.
46. K. Nozaki, W.-G. Li, T. Horiuchi, H. Takaya, T. Saito, A. Yoshida, K. Matsumura, Y Kato, T. Imai, T. Miura and H. Kumobayashi, J. Org. Chem. 61 (1996) 7658.
47. (a) D. Evans, J.A. Osborn and G. Wilkinson, J. Chem. Soc. A (1968) 3133;
48. (b) G. Yagupsky, C.K. Brown and G. Wilkinson, J. Chem. Soc. A (1970) 1392;
49. (c) C.K. Brown and G. Wilkinson, J. Chem. Soc. A (1970) 2753.
50. J.M. Brown and A.G. Kent, J. Chem. Soc., Perkin Trans. 2 (1987) 1597.
51. T. Horiuchi, E. Shirakawa, K. Nozaki and H. Takaya, Organometallics 16 (1997) 2981.
52. Other hybrid-type ligands have recently used for asymmetric hydroformylation, for example. (a) Y Pottier, A. Mortreux and F. Petit, J. Organomet. Chem. 370 (1989) 333;
53. (b) C.G. Arena, F. Nicoló, D. Drommi, G. Bruno and F. Faraone, J. Chem. Soc., Chem. Commun. (1994) 2251.
54. K. Nozaki, N. Sato, Y Tonomura, M. Yasutomi, H. Takaya, T. Hiyama, T. Matsubara and N. Koga, J. Am. Chem. Soc., in press.