Developing new chiral ferrocenyl ligands for asymmetric catalysis: A personal account

Chimia

Volumn 50, Issue 3, 1996, Pages 86-93

  Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

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EID: 0001898589     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (52)

1. For a recent review concerning classical Kyoto-type ligands, see: T. Hayashi, in 'Ferrocenes. Homogeneous Catalysis. Organic Synthesis. Materials Science.', Eds. A. Togni and T. Hayashi, VCH, Weinheim, 1995, p. 105-142.
2. Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chein. Soc. 1986, 108, 6405.
3. H. Allgeier, C. Angst, G. Bold, R.O. Duthaler, R. Heckendorn, A. Togni, Eur. Pat. Appl. EP 302 826 (Ciba-Geigy AG), Chem. Abstr. 1990, 112, 139 560g.
4. A. Togni, S.D. Pastor, Helv. Chim. Acta 1989, 72, 1038.
5. a) A. Togni, S.D. Pastor, Tetrahedron Lett. 1989, 30, 1071;
6. b) S.D. Pastor, A. Togni, J. Am. Chem. Soc. 1989, 111, 2333;
7. c) A. Togni, S.D. Pastor, G. Rihs, Helv. Chim. Acta 1989, 72, 1471;
8. d) A. Togni, S.D. Pastor, G. Rihs, J. Organomet. Chem. 1990, 381, C21;
9. e) S.D. Pastor, A. Togni, Tetrahedron Lett. 1990, 31, 839;
10. f) A. Togni, S.D. Pastor, J. Org. Chem. 1990, 55, 1649;
11. g) S.D. Pastor, A. Togni, Helv. Chim. Acta 1991, 74, 905;
12. h) A. Togni, S.D. Pastor, Chirality 1991, 3, 331;
13. i) A. Togni, P.S. Pregosin, R. Blumer, Helv. Chim. Acta 1991, 74, 1533;
14. j) S.D. Pastor, R. Kesselring, A. Togni, J. Organomet. Chem. 1992, 429, 415.
15. For a classical paper on the preparation of ferrocenyl ligands, see: T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamamoto, M. Kumada, Bull. Soc. Chem. Jpn. 1980, 53, 1138.
16. For a review on this particular topic, see: M. Sawamura, Y. Ito, Chem. Rev. 1992, 92, 857.
17. a) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153;
18. b) T. Hayashi, K. Hayashizaki, Y. Ito, Tetrahedron Lett. 1989, 30, 215.
19. G. Gokel, D. Marquarding, I. Ugi, J. Org. Chem. 1972, 37, 3052.
20. A. Togni, R. Häusel, Synlett 1990, 633.
21. J. Spencer, V. Gramlich, R. Häusel, A. Togni, Tetrahedron: Asymmetry 1996, 7, 41.
22. A. Togni, G. Rihs, R. E. Blumer, Organometallics 1992, 11, 613.
23. The idea of skipping the acetate intermediate and trying the direct substitution reaction of the dimethylamino group with, e.g., a secondary phosphine in acetic acid, was realized first by Heidi Landert at Ciba. See also: A. Togni, F. Spindler, N. Zanetti, A. Tijani, Eur. Pat. Appl. EP 0 564 406 A1 (Ciba-Geigy AG), Chem. Abstr. 1994, 121, P 35868h.
24. A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijani, J. Am. Chem. Soc. 1994, 116, 4062.
25. J. McGarrity, F. Spindler, R. Fuchs, M. Eyer, Eur. Pat. Appl. EP 624 587 A2, (Lonza AG), Chem. Abstr. 1995, 122, P81369q.
26. I thank Prof. B. Bosnich for a fruitful discussion on this topic.
27. a) A. Togni, F. Spindler, G. Rihs, N. Zanetti, M.C. Soares, T. Gerfin, V. Gramlich, Inorg. Chim. Acta 1994, 222, 213;
28. b) N.C. Zanetti, F. Spindler, J. Spencer, A. Togni, G. Rihs, Organometallics 1996, 15, 860.
29. H.C.L. Abbenhuis, U. Burckhardt, V. Gramlich, C. Köllner, R. Salzmann, P.S. Pregosin, A. Togni, Organometallics 1995, 14, 759.
30. For other successful chiral P,N-ligands recently reported, see, e.g.: a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614; ibid. Int. Ed. 1993, 32, 566;
31. For other successful chiral P,N-ligands recently reported, see, e.g.: a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614; ibid. Int. Ed. 1993, 32, 566;
32. b) P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht, G. Helmchen, Tetrahedron: Asymmetry 1994, 5, 573;
33. c) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769;
34. d) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, ibid. 1994, 35, 1523;
35. e) J.M. Brown, D.I. Hulmes, P.J. Guiry, Tetrahedron 1994, 50, 4493. For a recent review on N-containing ligands, see: A. Togni, L.M. Venanzi, Angew. Chem. 1994, 106, 517; ibid. Int. Ed. 1994, 33, 497.
36. e) J.M. Brown, D.I. Hulmes, P.J. Guiry, Tetrahedron 1994, 50, 4493. For a recent review on N-containing ligands, see: A. Togni, L.M. Venanzi, Angew. Chem. 1994, 106, 517; ibid. Int. Ed. 1994, 33, 497.
37. e) J.M. Brown, D.I. Hulmes, P.J. Guiry, Tetrahedron 1994, 50, 4493. For a recent review on N-containing ligands, see: A. Togni, L.M. Venanzi, Angew. Chem. 1994, 106, 517; ibid. Int. Ed. 1994, 33, 497.
38. For a review, see: J.K. Whitesell, Chem. Rev. 1989, 89, 1581.
39. See, e.g.: a) S. Trofimenko, Chem. Rev. 1993, 93, 943;
40. b) S. Trofimenko, Prog. Inorg. Chem. 1986, 34, 115.
41. U. Burckhardt, L. Hintermann, A. Schnyder, A. Togni, Organometallics 1995, 14, 5415.
42. A. Schnyder, L. Hintermann, A. Togni, Angew. Chem. 1995, 107, 996; ihid. Int. Ed. 1995, 34, 931.
43. A. Schnyder, L. Hintermann, A. Togni, Angew. Chem. 1995, 107, 996; ihid. Int. Ed. 1995, 34, 931.
44. A. Togni, U. Burckhardt, V. Gramlich, P.S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031.
45. Most structure elucidations in solution using 2D-NMR methods have been carried out in the group of my colleague Prof. P.S. Pregosin.
46. U. Burckhardt, unpublished results (part of the planned Ph.D thesis at ETH).
47. See, e.g.: S.C. Stinson, Chem. Eng. News 1994, September 19 issue, 38.
48. A collaboration with P. Blöchl (IBM Research Laboratories, Rüschlikon) has recently been started. Very promising results have been obtained from ab-initio molecular dynamics calculations (projector augmented wave method).
49. a) H.C.L. Abbenhuis, A. Togni, B. Müller, A. Albinati, U. Burckhardt, V. Gramlich, Organometallics 1994, 13, 4481;
50. b) H.C.L. Abbenhuis, U. Burckhardt, V. Gramlich, A. Martelletti, J. Spencer, I. Steiner, A. Togni, ibid. 1996, 15, in press.
51. P. Barbaro, A. Togni, manuscript in preparation. For the preparation of similar triphosphines, see: P. Barbaro, A. Togni, Organometallics 1995, 14, 3570.
52. P. Barbaro, A. Togni, manuscript in preparation. For the preparation of similar triphosphines, see: P. Barbaro, A. Togni, Organometallics 1995, 14, 3570.