Chiral diphosphites derived from D-glucose: New ligands for the asymmetric catalytic hydroformylation of vinyl arenes

Chemistry - A European Journal

Volumn 7, Issue 14, 2001, Pages 3086-3094

  Diéguez, Montserrat ^a   Pàmies, Oscar ^a   Ruiz, Aurora ^a   Castillón, Sergio ^a   Claver, Carmen ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Diphosphites; Hydroformylation; P ligands; Rhodium; Sugar derivatives

Indexed keywords

CATALYSIS; INFRARED SPECTROSCOPY; RHODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

GLUCOSE;

BIPHENYL DERIVATIVE; GLUCOSE; LIGAND; PHOSPHITE; POLYCYCLIC AROMATIC HYDROCARBON; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035898306     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010716)7:14<3086::AID-CHEM3086>3.0.CO;2-O     Document Type: Article

References (44)

1. a) M. Beller, B. Cornils, C. D. Frohning, C. W. Kohlpainter, J. Mol. Catal. 1995, 104, 17;
2. b) F. Agboussou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 95, 2485;
3. c) S. Gladiali, J. Bayón, C. Claver, Tetrahedron: Asymmetry 1995, 7, 1453.
4. d) Rhodium Catalyzed Hydroformylation (Eds.: P. W. N. M. van Leeuwen, C. Claver), Kluwer Academic Press, Dordrecht, 2000.
5. a) J. K. Stille, H. Su, P. Brechot, G. Parrinello, L. S. Hegedus, Organometallics 1991, 10, 1183;
6. b) G. Consiglio, S. C. A. Nefkens, A. Borer, Organometallics 1991, 10, 2046.
7. M. Diéguez, M. M. Pereira, A. M. Masdeu Bultó, C. Claver, J. C. Bayón, J. Mol. Catal. A: Chemical 1999, 143, 111, and references cited therein.
8. a) J. E. Babin, G. T. Whiteker (Union Carbide Chem. Plastics Techn. Co.) WO 93/03839, 1993
9. [Chem. Abs. 1993, 119, P159872 h];
10. b) G. J. H. Buisman, L. A. van der Veen, A. Klootwijk, W. G. J. der Lange, P. C. J. Kamer, P. W. N. M. van Leeuwen, D. Vogt, Organometallics 1997, 16, 2929.
11. a) K. Nozaki, N. Sakai, T. Nanno, T. Higashijima, S. Mano, T. Horiuchi, H. Takaya, J. Am. Chem. Soc. 1997, 119, 4413;
12. b) G. Franciò, W. Leitner, Chem. Commun. 1999, 1663.
13. a) J. S. Penne in Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995;
14. b) S. Hanessian in Total Synthesis of Natural Products: The "Chiron" Approach, Vol. 3, Pergamon, London, 1983.
15. For some recent applications see: a) M. Beller, J. G. E. Krauter, A. Zapf, Angew. Chem. 1997, 109, 793;
16. Angew. Chem. Int. Ed. Engl. 1997, 36, 772;
17. b) M. Reetz, S. R. Waldvogel, Angew. Chem. 1997, 109, 870;
18. Angew. Chem. Int. Ed. Engl. 1997, 36, 865;
19. c) K. Yonehara, T. Hashizume, K. Mori, K. Ohe, S. Uemura, Chem. Commun. 1999, 415;
20. d) T. V. RajanBabu, B, Radetich, K. K. You, T. A. Ayers, A. L. Casalnuovo, J. C. Calabrese, J. Org. Chem. 1999, 64, 3429,and references therein;
21. e) O. Pàmies, M. Diéguez, G. Net, A. Ruiz, C. Claver, Organometallics 2000, 19, 1488;
22. f) O. Pàmies, G. Net, A. Ruiz, C. Claver, Tetrahedron: Asymmetry 2000, 11, 1097;
23. g) O. Pàmies, G. Net, A. Ruiz, C. Claver, Eur. J. Inorg. Chem. 2000, 2011;
24. h) O. Pàmies, M. Diéguez, G. Net, A. Ruiz, C. Claver. Chem. Commun. 2000, 2383;
25. i) W. Li, Z. Zhang, D. Xiao, X. Zhang, J. Org. Chem., 2000, 65, 3489;
26. j) O. Pàmies, M. Diéguez, G. Net, A. Ruiz, C. Claver, Tetrahedron: Asymmetry 2000, 11, 4377.
27. G. J. H. Buisman, M. E. Martin, E. J. Vos, A. Klootwijk, P. C. J. Kamer, P. W. N. M. van Leeuwen, Tetrahedron: Asymmetry 1995, 6, 719.
28. The preliminary hydroformylation results with ligand 3 were partly reported in M. Diéguez, O. Pàmies, A. Ruiz, S. Castillón, C. Claver, Chem. Commun. 2000, 1607.
29. O.T. Schmidt in Methods in Carbohydrate Chemistry, Vol. 2, (Eds.: R. L. Whistler, M. L. Wolfrom), Academic Press, New York, 1963.
30. M. Nakjima, S. Takahashi, Agric. Biol. Chem. 1967, 31, 1079.
31. J. Hiebl, E. Zbiral, Monatsh. Chem. 1990, 121, 691.
32. The formation of 5,6-anhydrosugars from the corresponding mesylated compounds proceeds with low degrees of conversion (around 10%).
33. Phosphorochloridites are easily prepared in one step from the corresponding bisphenol as described in G. J. H. Buisman, P. C. J. Kamer, P. W. N. M. van Leeuwen, Tetrahedron: Asymmetry 1993, 4, 1625.
34. D. D. Pastor, S. P. Shum, R. K. Rodebaugh, A. D. Debellis, F. H. Clarke, Helv. Chim. Acta 1993, 76, 900.
35. a) H. Siegel, W. Himmele, Angew. Chem. 1980, 92, 182;
36. Angew. Chem. Int. Ed. Engl. 1980, 19, 178;
37. b) C. Botteghi, S. Paganelli, A. Schionato, M. Marchetti, Chirality 1991, 3, 355;
38. c) C. Botteghi, M. Marchetti, S. Paganelli in Transition Metals for Organic Synthesis, Vol. 1, (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998.
39. G. J. H. Buisman, E. J. Vos, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Chem. Soc. Dalton Trans. 1995, 409.
40. G. J. H. Buisman, L. A. van der Veen, E. J. Vos, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 1997, 16, 5681, and references therein.
41. P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H. Reek, P. Dierkes, Chem. Rev. 2000, 100, 2741, and references therein.
42. L. A. van der Veen, M. D. K. Boele, F. R. Bregman, P. C. J. Kamer, P. W. N. M. van Leeuwen, K. Goubitz, J. Fraanje, H. Schenk, C. Bo, J. Am. Chem. Soc. 1998, 120, 11616.
43. S. C. van der Slot, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Fraanje, K. Goubitz, M. Lutz, A. L. Spek, Organometallics 2000, 19, 2504.
44. For NMR characterization data see: M. J. Robins, Z. Guo, M. C. Samano, S. F. Wnuk, J. Am. Chem. Soc. 1999, 121, 1425.