Stereocontrolled preparation of stereocomplementary regioisomeric tricarbonyliron complexes in enantiopure form

Tetrahedron

Volumn 56, Issue 15, 2000, Pages 2273-2281

  Anson, Christopher E ^a   Dave, Gaurang ^a   Stephenson, G Richard ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Absolute configuration; Circular dichroism; Dienyl complexes; Enantioselective synthesis; Ferralactone; Tricarbonyliron

Indexed keywords

IRON COMPLEX; IRON DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; COMPLEX FORMATION; CONFERENCE PAPER; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0034615985     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01110-2     Document Type: Conference Paper

References (63)

1. Paiaro, G.; Palumbo, R.; Musco, A.; Panunzi. Tetrahedron Lett. 1965, 1067; Grubbs, R. H.; Grey, R. A. J. Chem. Soc., Chem. Commun. 1973, 77; Birch, A. J.; Bandara, B. M. R. Tetrahedron Lett. 1980, 21, 2981; Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett. 1981, 22, 1961; Bandara, B. M. R.; Birch, A. J.; Kelly, L. F.; Khor, T. C. Tetrahedron Lett. 1983, 24, 2191; Atton, J. G.; Evans, D. J.; Kane-Maguire, L. A. P.; Stephenson, G. R. J. Chem. Soc., Chem. Commun. 1984, 1246; Nakanishi, S.; Yamamoto, H.; Otsuji, Y.; Nakazumi, H. Tetrahedron Asymmetry 1993, 4, 1969; Howell, J. A. S.; Bell, A. G.; O'Leary, P. J.; McArdle, P.; Cunningham, D.; Stephenson, G. R.; Hastings, M. Organometallics 1994, 13, 1806
2. Paiaro, G.; Palumbo, R.; Musco, A.; Panunzi. Tetrahedron Lett. 1965, 1067; Grubbs, R. H.; Grey, R. A. J. Chem. Soc., Chem. Commun. 1973, 77; Birch, A. J.; Bandara, B. M. R. Tetrahedron Lett. 1980, 21, 2981; Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett. 1981, 22, 1961; Bandara, B. M. R.; Birch, A. J.; Kelly, L. F.; Khor, T. C. Tetrahedron Lett. 1983, 24, 2191; Atton, J. G.; Evans, D. J.; Kane-Maguire, L. A. P.; Stephenson, G. R. J. Chem. Soc., Chem. Commun. 1984, 1246; Nakanishi, S.; Yamamoto, H.; Otsuji, Y.; Nakazumi, H. Tetrahedron Asymmetry 1993, 4, 1969; Howell, J. A. S.; Bell, A. G.; O'Leary, P. J.; McArdle, P.; Cunningham, D.; Stephenson, G. R.; Hastings, M. Organometallics 1994, 13, 1806
3. Paiaro, G.; Palumbo, R.; Musco, A.; Panunzi. Tetrahedron Lett. 1965, 1067; Grubbs, R. H.; Grey, R. A. J. Chem. Soc., Chem. Commun. 1973, 77; Birch, A. J.; Bandara, B. M. R. Tetrahedron Lett. 1980, 21, 2981; Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett. 1981, 22, 1961; Bandara, B. M. R.; Birch, A. J.; Kelly, L. F.; Khor, T. C. Tetrahedron Lett. 1983, 24, 2191; Atton, J. G.; Evans, D. J.; Kane-Maguire, L. A. P.; Stephenson, G. R. J. Chem. Soc., Chem. Commun. 1984, 1246; Nakanishi, S.; Yamamoto, H.; Otsuji, Y.; Nakazumi, H. Tetrahedron Asymmetry 1993, 4, 1969; Howell, J. A. S.; Bell, A. G.; O'Leary, P. J.; McArdle, P.; Cunningham, D.; Stephenson, G. R.; Hastings, M. Organometallics 1994, 13, 1806
4. Paiaro, G.; Palumbo, R.; Musco, A.; Panunzi. Tetrahedron Lett. 1965, 1067; Grubbs, R. H.; Grey, R. A. J. Chem. Soc., Chem. Commun. 1973, 77; Birch, A. J.; Bandara, B. M. R. Tetrahedron Lett. 1980, 21, 2981; Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett. 1981, 22, 1961; Bandara, B. M. R.; Birch, A. J.; Kelly, L. F.; Khor, T. C. Tetrahedron Lett. 1983, 24, 2191; Atton, J. G.; Evans, D. J.; Kane-Maguire, L. A. P.; Stephenson, G. R. J. Chem. Soc., Chem. Commun. 1984, 1246; Nakanishi, S.; Yamamoto, H.; Otsuji, Y.; Nakazumi, H. Tetrahedron Asymmetry 1993, 4, 1969; Howell, J. A. S.; Bell, A. G.; O'Leary, P. J.; McArdle, P.; Cunningham, D.; Stephenson, G. R.; Hastings, M. Organometallics 1994, 13, 1806
5. Paiaro, G.; Palumbo, R.; Musco, A.; Panunzi. Tetrahedron Lett. 1965, 1067; Grubbs, R. H.; Grey, R. A. J. Chem. Soc., Chem. Commun. 1973, 77; Birch, A. J.; Bandara, B. M. R. Tetrahedron Lett. 1980, 21, 2981; Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett. 1981, 22, 1961; Bandara, B. M. R.; Birch, A. J.; Kelly, L. F.; Khor, T. C. Tetrahedron Lett. 1983, 24, 2191; Atton, J. G.; Evans, D. J.; Kane-Maguire, L. A. P.; Stephenson, G. R. J. Chem. Soc., Chem. Commun. 1984, 1246; Nakanishi, S.; Yamamoto, H.; Otsuji, Y.; Nakazumi, H. Tetrahedron Asymmetry 1993, 4, 1969; Howell, J. A. S.; Bell, A. G.; O'Leary, P. J.; McArdle, P.; Cunningham, D.; Stephenson, G. R.; Hastings, M. Organometallics 1994, 13, 1806
6. Paiaro, G.; Palumbo, R.; Musco, A.; Panunzi. Tetrahedron Lett. 1965, 1067; Grubbs, R. H.; Grey, R. A. J. Chem. Soc., Chem. Commun. 1973, 77; Birch, A. J.; Bandara, B. M. R. Tetrahedron Lett. 1980, 21, 2981; Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett. 1981, 22, 1961; Bandara, B. M. R.; Birch, A. J.; Kelly, L. F.; Khor, T. C. Tetrahedron Lett. 1983, 24, 2191; Atton, J. G.; Evans, D. J.; Kane-Maguire, L. A. P.; Stephenson, G. R. J. Chem. Soc., Chem. Commun. 1984, 1246; Nakanishi, S.; Yamamoto, H.; Otsuji, Y.; Nakazumi, H. Tetrahedron Asymmetry 1993, 4, 1969; Howell, J. A. S.; Bell, A. G.; O'Leary, P. J.; McArdle, P.; Cunningham, D.; Stephenson, G. R.; Hastings, M. Organometallics 1994, 13, 1806
7. Paiaro, G.; Palumbo, R.; Musco, A.; Panunzi. Tetrahedron Lett. 1965, 1067; Grubbs, R. H.; Grey, R. A. J. Chem. Soc., Chem. Commun. 1973, 77; Birch, A. J.; Bandara, B. M. R. Tetrahedron Lett. 1980, 21, 2981; Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett. 1981, 22, 1961; Bandara, B. M. R.; Birch, A. J.; Kelly, L. F.; Khor, T. C. Tetrahedron Lett. 1983, 24, 2191; Atton, J. G.; Evans, D. J.; Kane-Maguire, L. A. P.; Stephenson, G. R. J. Chem. Soc., Chem. Commun. 1984, 1246; Nakanishi, S.; Yamamoto, H.; Otsuji, Y.; Nakazumi, H. Tetrahedron Asymmetry 1993, 4, 1969; Howell, J. A. S.; Bell, A. G.; O'Leary, P. J.; McArdle, P.; Cunningham, D.; Stephenson, G. R.; Hastings, M. Organometallics 1994, 13, 1806
8. Paiaro, G.; Palumbo, R.; Musco, A.; Panunzi. Tetrahedron Lett. 1965, 1067; Grubbs, R. H.; Grey, R. A. J. Chem. Soc., Chem. Commun. 1973, 77; Birch, A. J.; Bandara, B. M. R. Tetrahedron Lett. 1980, 21, 2981; Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett. 1981, 22, 1961; Bandara, B. M. R.; Birch, A. J.; Kelly, L. F.; Khor, T. C. Tetrahedron Lett. 1983, 24, 2191; Atton, J. G.; Evans, D. J.; Kane-Maguire, L. A. P.; Stephenson, G. R. J. Chem. Soc., Chem. Commun. 1984, 1246; Nakanishi, S.; Yamamoto, H.; Otsuji, Y.; Nakazumi, H. Tetrahedron Asymmetry 1993, 4, 1969; Howell, J. A. S.; Bell, A. G.; O'Leary, P. J.; McArdle, P.; Cunningham, D.; Stephenson, G. R.; Hastings, M. Organometallics 1994, 13, 1806
9. Birch, A. J.; Kelly, L. F.; Narula, A. S. Tetrahedron 1982, 38, 1813; Pearson, A. J.; Khetani, V. D.; Roden, B. A. J. Org. Chem. 1989, 54, 5141.
10. Birch, A. J.; Kelly, L. F.; Narula, A. S. Tetrahedron 1982, 38, 1813; Pearson, A. J.; Khetani, V. D.; Roden, B. A. J. Org. Chem. 1989, 54, 5141.
11. Birch, A. J.; Raverty, W. D.; Stephenson, G. R.; Organometallics 1984, 3, 1075; Maywald, F.; Eilbracht, P. Synlett 1996, 380; Knölker, H.-J.; Hermann, H. Angew. Chem. Int. Ed. Engl. 1996, 35, 341.
12. Birch, A. J.; Raverty, W. D.; Stephenson, G. R.; Organometallics 1984, 3, 1075; Maywald, F.; Eilbracht, P. Synlett 1996, 380; Knölker, H.-J.; Hermann, H. Angew. Chem. Int. Ed. Engl. 1996, 35, 341.
13. Birch, A. J.; Raverty, W. D.; Stephenson, G. R.; Organometallics 1984, 3, 1075; Maywald, F.; Eilbracht, P. Synlett 1996, 380; Knölker, H.-J.; Hermann, H. Angew. Chem. Int. Ed. Engl. 1996, 35, 341.
14. Roush, W. R.; Park, J. C. Tetrahedron Lett. 1990, 31, 4707; Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151.
15. Roush, W. R.; Park, J. C. Tetrahedron Lett. 1990, 31, 4707; Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151.
16. Takemoto, Y.; Baba, Y.; Honda, A.; Nakao, S.; Noguchi, I.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron 1998, 54, 15567; Tanaka, K.; Watanabe, T.; Shimamoto, K.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599.
17. Takemoto, Y.; Baba, Y.; Honda, A.; Nakao, S.; Noguchi, I.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron 1998, 54, 15567; Tanaka, K.; Watanabe, T.; Shimamoto, K.; Sahakitpichan, P.; Fuji, K. Tetrahedron Lett. 1999, 40, 6599.
18. Alcock, N. W.; Crout, D. H. G.; Henderson, C. M.; Thomas, S. E. J. Chem. Soc., Chem. Commun. 1988, 746; Uemura, M.; Nishimura, H.; Yamada, S.; Hayashi, Y.; Nakamura, K.; Ishihara, K.; Ohno, A. Tetrahedron Asym. 1994, 5, 1673; Howell, J. A. S.; O'Leary, P. J.; Palin, M. G.; Jaouen, G.; Top, S. Tetrahedron Asymmetry 1996, 7, 307.
19. Alcock, N. W.; Crout, D. H. G.; Henderson, C. M.; Thomas, S. E. J. Chem. Soc., Chem. Commun. 1988, 746; Uemura, M.; Nishimura, H.; Yamada, S.; Hayashi, Y.; Nakamura, K.; Ishihara, K.; Ohno, A. Tetrahedron Asym. 1994, 5, 1673; Howell, J. A. S.; O'Leary, P. J.; Palin, M. G.; Jaouen, G.; Top, S. Tetrahedron Asymmetry 1996, 7, 307.
20. Alcock, N. W.; Crout, D. H. G.; Henderson, C. M.; Thomas, S. E. J. Chem. Soc., Chem. Commun. 1988, 746; Uemura, M.; Nishimura, H.; Yamada, S.; Hayashi, Y.; Nakamura, K.; Ishihara, K.; Ohno, A. Tetrahedron Asym. 1994, 5, 1673; Howell, J. A. S.; O'Leary, P. J.; Palin, M. G.; Jaouen, G.; Top, S. Tetrahedron Asymmetry 1996, 7, 307.
21. Knölker H.-J., Herzberg D. Tetrahedron Lett. 40:1999;3547.
22. Stephenson G.R., Howard P.W. J. Organometal. Chem. 370:1989;97.
23. Stephenson, G. R.; Howard, P. W.; Taylor, S. C. J. Organometal. Chem. 1985, 285, C17; Pearson, A. J.; Gelormini, A. M.; Pinkerton, A. A. Organometallics 1992, 11, 936.
24. Stephenson, G. R.; Howard, P. W.; Taylor, S. C. J. Organometal. Chem. 1985, 285, C17; Pearson, A. J.; Gelormini, A. M.; Pinkerton, A. A. Organometallics 1992, 11, 936.
25. Ley S.V., Cox L.R., Meek G., Metten K.-H., Piqué C., Worrall J.M. J. Chem. Soc., Perkin Trans. 1. 1997;3299.
26. Ley S.V., Cox L.R. J. Chem. Soc., Perkin Trans. 1. 1997;3315.
27. Ley, S. V.; Cox, L. R. Chem. Commun. 1998, 227; Ley, S. V.; Burckhardt, S.; Cox, L. R.; Worrall, J. M. Chem. Commun. 1998, 229.
28. Ley, S. V.; Cox, L. R. Chem. Commun. 1998, 227; Ley, S. V.; Burckhardt, S.; Cox, L. R.; Worrall, J. M. Chem. Commun. 1998, 229.
29. Ley S.V., Cox L.R., Middleton B., Worrall J.M. Tetrahedron. 55:1999;3515.
30. Ley, S. V.; Meek, G. J. Chem. Soc., Chem. Commun. 1995, 1751; Bates, R. W.; Fernández-Megía, E.; Ley, S. V.; Rück-Braun, K.; Tilbrook, D. M. G. J. Chem. Soc., Perkin Trans., 1 1997, 1917.
31. Ley, S. V.; Meek, G. J. Chem. Soc., Chem. Commun. 1995, 1751; Bates, R. W.; Fernández-Megía, E.; Ley, S. V.; Rück-Braun, K.; Tilbrook, D. M. G. J. Chem. Soc., Perkin Trans., 1 1997, 1917.
32. Aumann R., Ring H., Kruger C., Goddard R. Chem. Ber. 112:1979;3644.
33. Ley S.V., Cox L.R., Meek G., Metten K.-H., Piqué C. J. Chem. Soc., Chem. Commun. 1994;1931.
34. Böhmer J., Hampel F., Schobert R. Synthesis. 1999;661.
35. Becker H., Soler M.A., Sharpless K.B. Tetrahedron. 51:1995;1345.
36. Kolb H.C., Sharpless K.B. Tetrahedron. 48:1992;10515.
37. Dave, G. PhD thesis; University of East Anglia: Norwich, 1997.
38. Ley S.V., Burckhardt S., Cox L.R., Meek G. J. Chem. Soc., Perkin Trans. 1. 1997;3327.
39. Horton A.M., Ley S.V. J. Organometal. Chem. 285:1985;C17.
40. Horton A.M., Hollinshead D.M., Ley S.V. Tetrahedron. 40:1984;1737.
41. Howell J.A.S., O'Leary P.J., Palin M.G., Jaouen G., Top S. Tetrahedron Asymmetry. 7:1996;307.
42. Graf R.E., Lillya C.P. J. Organometal. Chem. 166:1979;53.
43. The assignment is based on the fact that both the sign of specific rotation and the absolute configuration are known for a deuterium-labelled sample with a CHD group at C-1; see Ref. 24.
44. Howell J.A.S., Palin M.G., Jaouen G., Top S., El Hafa H., Cense J.M. Tetrahedron Asymmetry. 4:1993;1241.
45. Djedaini F., Grée D., Martelli J., Grée R., Leroy L., Bolard J., Toupet L. Tetrahedron Lett. 30:1989;3781.
46. Stephenson G.R., Howard P.W. J. Chem. Soc., Perkin Trans. 1. 1994;2873.
47. * nomenclature.
48. * nomenclature.
49. Grée, R.; Laabassi, M.; Mosset, P.; Carrié, R. Tetrahedron Lett. 1984, 25, 3693; Teniou, A.; Toupet, L.; Grée, R. Synlett 1991, 195; Nunn, K.; Mosset, P.; Gree, R.; Saalfrank, R. W.; Peters, K.; von Schnering, H. G. Angew. Chem. Int. Ed. Engl. 1992, 31, 224; Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505.
50. Grée, R.; Laabassi, M.; Mosset, P.; Carrié, R. Tetrahedron Lett. 1984, 25, 3693; Teniou, A.; Toupet, L.; Grée, R. Synlett 1991, 195; Nunn, K.; Mosset, P.; Gree, R.; Saalfrank, R. W.; Peters, K.; von Schnering, H. G. Angew. Chem. Int. Ed. Engl. 1992, 31, 224; Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505.
51. Grée, R.; Laabassi, M.; Mosset, P.; Carrié, R. Tetrahedron Lett. 1984, 25, 3693; Teniou, A.; Toupet, L.; Grée, R. Synlett 1991, 195; Nunn, K.; Mosset, P.; Gree, R.; Saalfrank, R. W.; Peters, K.; von Schnering, H. G. Angew. Chem. Int. Ed. Engl. 1992, 31, 224; Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505.
52. Grée, R.; Laabassi, M.; Mosset, P.; Carrié, R. Tetrahedron Lett. 1984, 25, 3693; Teniou, A.; Toupet, L.; Grée, R. Synlett 1991, 195; Nunn, K.; Mosset, P.; Gree, R.; Saalfrank, R. W.; Peters, K.; von Schnering, H. G. Angew. Chem. Int. Ed. Engl. 1992, 31, 224; Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505.
53. Frank-Neumann, M.; Chemla, P.; Martina, D. Synlett 1990, 641; Takemoto, Y.; Takeuchi, J.; Iwata, C. Tetrahedron Lett. 1993, 34, 6067; Frank-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett. 1997, 38, 4469.
54. Frank-Neumann, M.; Chemla, P.; Martina, D. Synlett 1990, 641; Takemoto, Y.; Takeuchi, J.; Iwata, C. Tetrahedron Lett. 1993, 34, 6067; Frank-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett. 1997, 38, 4469.
55. Frank-Neumann, M.; Chemla, P.; Martina, D. Synlett 1990, 641; Takemoto, Y.; Takeuchi, J.; Iwata, C. Tetrahedron Lett. 1993, 34, 6067; Frank-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett. 1997, 38, 4469.
56. 1 0.0337 (I≥2σ(I)); Flack χ=0.02(5). Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre, reference 136759.
57. Ley S.V., Meek G. Chem. Commun. 1996;317.
58. A long-standing strategic objective in our work is the demonstration of routes to specific dienyl complexes without recourse to chromatography so that they can be made easily available on a large scale; for an example in the cyclohexadienyl series, see: Meng, W. D.; Stephenson, G. R. J. Organometal. Chem. 1989, 371, 355.
59. Howell J.A.S., Squibb A.D., Bell A.G., McArdle P., Langerman D.H., Gree R. Organometallics. 13:1994;4336.
60. Schotten, C. Ber. 1884, 17, 2544; Baumann, Ber. 1886, 19, 3218.
61. Schotten, C. Ber. 1884, 17, 2544; Baumann, Ber. 1886, 19, 3218.
62. Mahler J.E., Pettit R. J. Am. Chem. Soc. 85:1963;3955.
63. Greaves E.O., Knox G.R., Pauson P.L. J. Chem. Soc., Chem. Commun. 1969;1124.