Chiral base mediated asymmetric synthesis of tricarbonyl(η6-arene)-chromium complexes

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1997, Pages 401-415

  Ewin, Richard A ^a   MacLeod, Angus M ^b   Price, David A ^a   Simpkins, Nigel S ^a   Watt, Alan P ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748668254     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a605812d     Document Type: Article

References (58)

1. For reviews, see: (a) F. J. McQuillin, D. G. Parker and G. R. Stephenson, Transition Metal Organometallics for Organic Synthesis, Cambridge University Press, 1991;
2. (b) M. F. Semmelhack, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 4, p. 517;
3. (c) M. F. Semmelhack, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Elsevier Science Ltd, Oxford, 1995, vol. 12, p. 1017;
4. (d) S. G. Davies and T. D. McCarthy, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Elsevier Science Ltd, Oxford, 1995, vol. 12, p. 1039.
5. For examples, see (a) J-F. Carpentier, L. Pamart, L. Maciewjeski, Y. Castanet, J. Brocard and A. Mortreux, Tetrahedron Lett., 1996, 37, 167;
6. (b) M. Uemura, H. Nishimura, S. Yamada, Y. Hayashi, K. Nakamura, K. Ishihara and A. Ohno, Tetrahedron:Asymmetry, 1994, 5, 1673;
7. (c) C. Baldoni, S. Maiorana, G. Carrea and S. Riva, Tetrahedron: Asymmetry, 1993, 4, 767.
8. See: (a) H-G. Schmalz, B. Millies, J. W. Bats and G. Durner, Angew. Chem., Int. Ed. Engl., 1992, 31, 631;
9. (b) M. Uemura, R. Miyake, K. Nakayama, M. Shiro and Y. Hayashi, J. Org. Chem., 1993, 58, 1238;
10. (c) A. Alexakis, P. Mangeney, I. Marek, F. Rose-Munch, E. Rose, A. Semra and F. Robert, J. Am. Chem. Soc., 1992, 114, 8288;
11. (d) A. Alexakis, T. Kanger, P. Mangeney, F. Rose-Munch, A. Perrotey and E. Rose, Tetrahedron:Asymmetry, 1995, 6, 47.
12. (a) Y. Kondo, J. R. Green and J. Ho, J. Org. Chem., 1991, 56, 7199;
13. (b) Y. Kondo, J. R. Green and J. Ho. J. Org. Chem., 1991, 58, 6182;
14. (c) A. Alexakis, T. Kanger, P. Mangeney, F. Rose-Munch, A. Perrotey and E. Rose, Tetrahedron:Asymmetry, 1995, 6, 47;
15. (d) S. G. Davies and W. E. Hume, J. Chem. Soc., Chem. Commun., 1995, 251;
16. (e) S. G. Davies, T. Loveridge and J. M. Clough, J. Chem. Soc., Chem. Commun., 1995, 817.
17. (a) M. Uemura, H. Nishimura and T. Hayashi, Tetrahedron Lett., 1993, 34, 107;
18. (b) M. Uemura, H. Nishimura and T. Hayashi, J. Organomet. Chem., 1994, 473, 129.
19. See for examples (a) E. P. Kündig, R. Liu and A. Ripa, Helv. Chim. Acta, 1992, 75, 2657;
20. (b) R. P. Hsung and W. D. Wulff, J. Am. Chem. Soc., 1994, 116, 6449;
21. (c) J. A. S. Howell, M. G. Palin, G. Jaouen, B. Malezieux, S. Top, J. M. Cense, J. Salaun, P. McArdle, D. Cunningham and M. O'Gara, Tetrahedron:Asymmetry, 1996, 7, 95;
22. (d) P. W. N. Christian, R. Gil, K. Muniz-Fernández, S. E. Thomas and A. T. Wierzchleyski, J. Chem. Soc., Chem. Commun., 1994, 1569;
23. (e) S. L. Griffiths, S. Perrio and S. E. Thomas, Tetrahedron:Asymmetry, 1994, 5, 1847.
24. D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Watt, J. Org. Chem., 1994, 59, 1961.
25. D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Watt, Tetrahedron Lett., 1994, 35, 6159.
26. R. A. Ewin and N. S. Simpkins, Synlett, 1996, 317.
27. E. P. Kündig and A. Quattropani, Tetrahedron Lett., 1994, 35, 3497.
28. H-G. Schmalz and K. Schelihaas, Tetrahedron Lett., 1995, 36, 5515.
29. M. Uemura, Y. Hayashi and Y. Hayashi, Tetrahedron:Asymmetry, 1994, 5, 1427.
30. E. L. M. Cowton, S. E. Gibson, M. J. Schneider and M. H. Smith, Chem. Commun., 1996, 839.
31. (a) P. J. Cox and N. S. Simpkins, Tetrahedron:Asymmetry, 1991, 2, 1; for more recent contributions, see:
32. (b) N. J. Newcombe and N. S. Simpkins, J. Chem. Soc., Chem. Commun., 1995, 831;
33. (c) D. M. Hodgson and A. R. Gibbs, Tetrahedron:Asymmetry, 1996, 7, 407;
34. (d) D. I. MaGee, S. Setiadji and R. A. Martin, Tetrahedron: Asymmetry, 1995, 6, 639;
35. (e) D. Price and N. S. Simpkins, Tetrahedron Lett., 1995, 36, 6135.
36. L. A. Bromley, S. G. Davies and C. L. Goodfellow, Tetrahedron: Asymmetry, 1991, 2, 139.
37. F. Effenburger and K. Schöllkopf, Chem. Ber., 1985, 118, 4356.
38. S. G. Davies and C. L. Goodfellow, J. Chem. Soc., Perkin Trans. 1, 1990, 393.
39. (a) B. J. Bunn, N. S. Simpkins, Z. Spavold and M. J. Crimmin, J. Chem. Soc., Perkin Trans. 1, 1993, 3113;
40. (b) M. Majewski, R. Lazny and P. Nowak, Tetrahedron Lett., 1995, 36, 5465;
41. (c) see also B. H. Lipshutz, M. R. Wood and C. W. Lindsley, Tetrahedron Lett., 1995, 36, 4385.
42. D. B Collum, Acc. Chem. Res., 1993, 26, 227.
43. 6-arene)chromium complexes has been observed previously, see for example ref. 4(6). See also E. P. Kundig, C. Grivet and S. Spichiger, J. Organomet. Chem., 1987, 332, C13; Dr D. Widdowson, personal communication.
44. D. L. Comins and J. D. Brown, J. Org. Chem., 1984, 49, 1079.
45. A. Alexakis, T. Kanger, P. Mangeney, F. Rose-Munch, A. Perrotey and E. Rose, Tetrahedron:Asymmetry, 1995, 6, 2135.
46. (a) R. J. Card and W. S. Trahanovsky, J. Org. Chem., 1980, 45, 2560;
47. (b) G. Jaouen, S. Top, A. Laconi, D. Couturier and J. Brocard, J. Am. Chem. Soc., 1984, 106, 2207;
48. (c) M. F. Semmelhack, J. Bisaha and M. Czarny, J. Am. Chem. Soc., 1979, 101, 768;
49. (d) G. Simonneaux and G. Jaouen, Tetrahedron, 1979, 35, 2249;
50. (e) M. C. Sénéchal-Tocquer, D. Sénéchal, J. Y. Le Bihan, D. Centric and B. Caro, Bull. Soc. Chim. Fr., 1992, 129, 121.
51. S. J. Coote, S. G. Davies, D. Middlemiss and A. Naylor, J. Organomet. Chem., 1989, 379, 81.
52. (a) U. Nagai, T. Shishido, R. Chiba and H. Mitsuhashi, Tetrahedron, 1965, 21, 1701;
53. (b) H. Takahashi, T. Tsubuki and K. Higashiyama, Chem. Pharm. Bull., 1991, 3136.
54. P. H. J. Carlsen, T. Katsuki, V. S. Martin and K. B. Sharpless, J. Org. Chem., 1981, 46, 3936.
55. K. Bambridge, M. J. Begley and N. S. Simpkins, Tetrahedron Lett., 1994, 35, 3391.
56. J. Blagg, S. G. Davies, C. L. Goodfellow and K. H. Sutton, J. Chem. Soc., Perkin Trans. 1, 1987, 1805.
57. C. A. L. Mahaffy and P. L. Pauson, Inorg. Synth., 1979, 19, 154.
58. M. F. Semmelhack and A. Zask, J. Am. Chem. Soc., 1983, 105, 2034.