Transition metal fluoride complexes in asymmetric catalysis

Chemistry - A European Journal

Volumn 5, Issue 12, 1999, Pages 3437-3442

  Pagenkopf, Brian L ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Asymmetric catalysis; Bridging ligands; Fluorine; Transition metals

Indexed keywords

EID: 85087245209     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19991203)5:12<3437::aid-chem3437>3.3.co;2-5     Document Type: Article

References (77)

1. For representative examples, see: a) D. A. Evans, J. A. Murry, P. Von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 964; Angew. Chem. Int. Ed. Engl. 1995, 34, 798;
2. For representative examples, see: a) D. A. Evans, J. A. Murry, P. Von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 964; Angew. Chem. Int. Ed. Engl. 1995, 34, 798;
3. b) D. J. R. O'Mahony, D. B. Belanger, T. Livinghouse, Synlett 1998, 4, 443.
4. a) E. F. Murphy, R. Murugavel, H. W. Roesky, Chem. Rev. 1997, 97, 3425;
5. b) M. G. Walawalkar, R. Murugavel, H. W. Roesky, Eur. J. Solid. State. Chem. 1996, 33, 943;
6. M. Witt, H. W. Roesky, in Progress in Inorganic Chemistry, Vol. 40, (Ed: S. J. Lippard), Wiley, 1992.
7. N. M. Doherty, N. W. Hoffman, Chem. Rev. 1991, 91, 553.
8. 2 in enantioselective Pt-catalyzed hydroformylation, see: L. Kollar, T. Kegl, J. Bakos, J. Organomet. Chem. 1993, 453, 155.
9. For a review that provides entry into this area, see: R. O. Duthaler, A. Hafner, Angew. Chem. 1997, 109, 43; Angew. Chem. Int. Ed. Engl. 1997, 36, 43.
10. For a review that provides entry into this area, see: R. O. Duthaler, A. Hafner, Angew. Chem. 1997, 109, 43; Angew. Chem. Int. Ed. Engl. 1997, 36, 43.
11. L. Pauling, The Nature of the Chemial Bond, Cornell, 1960, 3rd ed., pp. 317-320.
12. F. A. Cotton, G. Wilkinson, C. A. Murillo, M. Bochman, Advanced Inorganic Chemistry, Wiley, New York, 1999, p. 165.
13. V. Jonas, G. Frenking, M. T. Reetz, J. Am. Chem. Soc. 1994, 116, 8741.
14. L. Vaska, J. Peone, J. Chem. Soc. Chem. Commun. 1971, 418.
15. G. Frenking, S. Fau, C. M. Marchand, H. Grützmacher, J. Am. Chem. Soc. 1997, 119, 6648.
16. G. A. Olah, G. Rasul, L. Heiliger, G. K. S. Prakash, J. Am. Chem. Soc. 1996, 118, 3580.
17. J. Kapp, C. Schade, A. M. El-Nahas, P. von R. Schleyer, Angew. Chem. 1996, 108, 2373; Angew. Chem. Int. Ed. Engl. 1996, 35, 2236.
18. J. Kapp, C. Schade, A. M. El-Nahas, P. von R. Schleyer, Angew. Chem. 1996, 108, 2373; Angew. Chem. Int. Ed. Engl. 1996, 35, 2236.
19. Curiously, however, the participation of organofluorides in hydrogen bonding is a rarity. For an superb discussion, see: J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89.
20. D. M. Branan, N. W. Hoffman, E. A. McElroy, N. C. Miller, D. L. Ramage, A. F. Scholt, S. H. Young, Inorg. Chem. 1987, 26, 2915.
21. J. P. Flemming, M. C. Pilon, O. Y. Borbulevitch, M. Y. Antipin, V. V. Grushin, Inorg. Chim. Acta 1998, 280, 87.
22. D. J. Gulliver, W. Levason, M. Webster, Inorg. Chim. Acta 1981, 523, 153.
23. P. Yu, M. L. Montero, C. E. Barnes, H. W. Roesky, I. Uson, Inorg. Chem. 1998, 37, 2595.
24. This insolubility stems inpart from the fact that transition metal fluorides tend to be polymeric solids that form long chainlike structures through bridging fluoride ligands.
25. M. G. Walawalkar, R. Murugavel, H. W. Roesky, Eur. J. Solid State Inorg. Chem. 1996, 33, 943.
26. R. Noyori, I. Nishida, J. Sakata, J. Am. Chem. Soc. 1983, 105, 1598.
27. a) K. O. Christe, W. W. Wilson, R. D. Wilson, R. Bau, J.-A. Feng, J. Am. Chem. Soc. 1990, 112, 7619;
28. b) R. Z. Gnann, R. I. Wagner, K. O. Christe, R. Bau, G. A. Olah, W. W. Wilson, J. Am. Chem. Soc. 1997, 119, 112.
29. R. Schwesinger, R. Link, G. Thiele, H. Rotter, D. Honert, H.-H. Limbach, F. Männle, Angew. Chem. 1991, 103, 1376; Angew. Chem. Int. Ed. Engl. 1991, 30, 1372.
30. R. Schwesinger, R. Link, G. Thiele, H. Rotter, D. Honert, H.-H. Limbach, F. Männle, Angew. Chem. 1991, 103, 1376; Angew. Chem. Int. Ed. Engl. 1991, 30, 1372.
31. a) M. Gingras, Tetrahedron Lett. 1991, 32, 7381;
32. b) A. S. Pilcher, H. L. Ammon, P. DeShong, J. Am. Chem. Soc. 1995, 117, 5166.
33. a) H. Schnutenhaus, H. H. Brintzinger, Angew. Chem. 1979, 91, 837; Angew. Chem. Int. Ed. Engl. 1979, 18, 777;
34. a) H. Schnutenhaus, H. H. Brintzinger, Angew. Chem. 1979, 91, 837; Angew. Chem. Int. Ed. Engl. 1979, 18, 777;
35. b) F. R. W. P. Wild, L. Zsolnai, G. Huttner, H. H. Brintzinger, J. Organomet. Chem. 1982, 232, 233.
36. X. Verdaguer, U. E. W. Lange, M. T. Reding, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 6784.
37. a) M. E. Vol'pin, V.B. Sure, Nature, 1966, 209, 1236;
38. b) H. H. Brintzinger, J. Am. Chem. Soc. 1966, 88, 4305;
39. H. H. Brintzinger, J. Am. Chem. Soc. 1966, 88, 4307.
40. a) E. M. Carreira, R. A. Singer, W. S. Lee, J. Am. Chem. Soc. 1994, 116, 8837;
41. b) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 116, 12360;
42. R. A. Singer, E. M. Carreria, Tetrahedron Lett. 1997, 38, 927.
43. T. Mukaiyama, K. Banno, K. Narasaka, J. Am. Chem. Soc. 1974, 96, 7503.
44. This strategy has been examined in pioneering work with achiral rhodium enolates by Heathcock and Bergman: G. A. Slough, R. G. Bergman, C. H. Heathcock, J. Am. Chem. Soc. 1989, 111, 938.
45. B. L. Pagenkopf, J. Krüger, A. Stojanovic, E. M. Carreira, Angew. Chem. 1998, 110, 3312; Angew. Chem. Int. Ed. 1998, 37, 3124.
46. B. L. Pagenkopf, J. Krüger, A. Stojanovic, E. M. Carreira, Angew. Chem. 1998, 110, 3312; Angew. Chem. Int. Ed. 1998, 37, 3124.
47. J. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837.
48. J. Krüger, E. M. Carreira, Tetrahedron Lett. 1998, 39, 7013.
49. R. Dorta, P. Egli, F. Zürcher, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857.
50. Often a strong base, such as lithium anilide (LiNHPh), is required to promote the condensation of aniline with norbornene 15 under transition metal catalysis, but lithium anilide completely suppressed the catalytic activity of these iridium complexes.
51. U. Burckhardt, M. Baumann, A. Togni, Tetrahedron: Asymmetry 1997, 8, 155.
52. a) K. Ishihara, M. Mouri, Q. Z. Gao, T. Maruyama, K. Furuta, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 11490;
53. b) S. Aoki, M. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783.
54. H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990; Angew. Chem. Int. Ed. Engl. 1994, 33, 938.
55. H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990; Angew. Chem. Int. Ed. Engl. 1994, 33, 938.
56. D. R. Gauthier, Jr., E. M. Carreira, Angew. Chem. 1996, 108, 2521; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363.
57. D. R. Gauthier, Jr., E. M. Carreira, Angew. Chem. 1996, 108, 2521; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363.
58. a) For a recent lead reference for diethylzinc additions, see: J. Qiu, C. Guo, X. M. Zhang, J. Org. Chem. 1997, 62, 2665;
59. b) K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833;
60. R. Noyori, M. Kitamura, Angew. Chem. 1990, 30, 34; Angew. Chem. Int. Ed. Engl. 1991, 30, 49.
61. R. Noyori, M. Kitamura, Angew. Chem. 1990, 30, 34; Angew. Chem. Int. Ed. Engl. 1991, 30, 49.
62. 3Al (3 equiv): A. S. C. Chan, F.-Y. Zhang, C.-W. Yip, J. Am. Chem. Soc. 1997, 119, 4080.
63. N. Minowa, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1987, 60, 3697.
64. a) D. Seebach, A. K. Beck, B. Schmidt, Y. M. Wang, Tetrahedron 1994, 50, 4363;
65. b) B. Weber, D. Seebach, Tetrahedron 1994, 50, 6117;
66. B. Weber, D. Seebach, Tetrahedron 1994, 50 7473;
67. D. Seebach, D. Plattner, A. K. Beck, Y. M. Wang, D. Hunziker, W. Petter, Helv. Chim. Acta 1992 75, 2171;
68. e) B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 1383; Angew. Chem. Int. Ed. Engl. 1991 30, 1321.
69. e) B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 1383; Angew. Chem. Int. Ed. Engl. 1991 30, 1321.
70. a) M. J. Rozema, A. Sidduri, P. Knochel, J. Org. Chem. 1992, 57, 1956;
71. b) M. J. Rozema, C. Eisenberg, H. Lütjens, R. Ostwald, K. Belyk, P. Knochel, Tetrahedron Lett. 1993, 34, 3115;
72. W. Brieden, R. Ostwald, P. Knöchel, Angew. Chem. 1993, 105, 629; Angew. Chem. Int. Ed. Engl. 1993, 32, 582;
73. W. Brieden, R. Ostwald, P. Knöchel, Angew. Chem. 1993, 105, 629; Angew. Chem. Int. Ed. Engl. 1993, 32, 582;
74. C. K. Reddy, P. Knochel, Angew. Chem. 1996, 108, 1812; Angew. Chem. Int. Ed. Engl 1996, 35, 1700.
75. C. K. Reddy, P. Knochel, Angew. Chem. 1996, 108, 1812; Angew. Chem. Int. Ed. Engl 1996, 35, 1700.
76. B. L. Pagenkopf, E. M. Carreira, Tetrahedron Lett. 1998, 39, 9593.
77. T. Ooi, N. Kagoshima, K. Maruoka, J. Am. Chem. Soc. 1997, 119, 5754.