Transition metal complexes in organic synthesis. Part 47.¹ Organic synthesis via tricarbonyl(η⁴-diene)iron complexes

Abstract

The protection of conjugated dienes by coordination to the tricarbonyliron fragment offers many potential applications of the resulting complexes to organic synthesis. The preparation of tricarbonyl(η⁴-1,3-diene)iron complexes is readily achieved by a 1-azabutadiene-catalyzed complexation of the free ligands. An asymmetric catalytic complexation of prochiral cyclohexa-1,3-dienes with pentacarbonyl-iron using chiral 1-azabutadienes affords chiral nonracemic complexes. The chiral tricarbonyliron complexes of acyclic butadienes represent versatile starting materials for the synthesis of a broad range of polyunsaturated natural products. Consecutive carbon–carbon and carbon–nitrogen bond formations of the tricarbonyliron–cyclohexa-1,3-diene complexes and arylamines provide many biologically active carbazole alkaloids and a tetracyclic subunit of the discorhabdin alkaloids. The iron-mediated [2+2+1] cycloaddition of trimethylsilylacetylenes and carbon monoxide affords stable 2,5-bis(trimethylsilyl)-substituted cyclopentadienones which are useful substrates for further cycloadditions.

References

1. Part 46: H.-J. Knölker, M. Graf and U. Mangei, J. Prakt. Chem., 1998, 340, 530.
2. A. J. Pearson, Iron Compounds in Organic Synthesis, Academic Press, London, 1994, chap. 4 and 5; and references cited therein.
3. R. Grée and J. P. Lellouche, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich (CT), 1995, vol. 4, p. 129; and references cited therein.
4. H.-J. Knölker, Synlett, 1992, 371 and references cited therein.
5. H.-J. Knölker, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, Chichester, 1995, vol. 1, p. 333; and references cited therein.
6. H.-J. Knölker, G. Baum, N. Foitzik, H. Goesmann, P. Gonser, P. G. Jones and H. Röttele, Eur. J. Inorg. Chem., 1998, 993.
7. H.-J. Knölker, E. Baum, P. Gonser, G. Rohde and H. Röttele, Organometallics, 1998, 17, 3916.
8. H.-J. Knölker and H. Hermann, Angew. Chem., 1996, 108, 363 (Angew. Chem., Int. Ed. Engl., 1996, 35, 341).
9. M. Franck-Neumann, M. Sedrati and M. Mokhi, Angew. Chem., 1986, 98, 1138 (Angew. Chem., Int. Ed. Engl., 1986, 25, 1131).
10. M. Franck-Neumann and P.-J. Colson, Synlett, 1991, 891.
11. A. Monpert, J. Martelli, R. Grée and R. Carrié, Tetrahedron Lett., 1981, 22, 1961.
12. C. Tao and W. A. Donaldson, J. Org. Chem., 1993, 58, 2134.
13. W. A. Donaldson, P. T. Bell, Z. Wang and D. W. Bennett, Tetrahedron Lett., 1994, 32, 5892; V. Prahlad and W. A. Donaldson, Tetrahedron Lett., 1996, 37, 9169.
14. T. J. Benvegnu, L. J. Toupet and R. Grée, Tetrahedron, 1996, 52, 11811; T. J. Benvegnu and R. Grée, Tetrahedron, 1996, 52, 11821.
15. C. Iwata and Y. Takemoto, Chem. Commun., 1996, 2497 and references cited therein.
16. D. P. Chakraborty, in The Alkaloids, ed. A. Brossi, Academic Press, New York, 1993, vol. 44, p. 257; and references cited therein.
17. H.-J. Knölker, in Advances in Nitrogen Heterocycles, ed. C. J. Moody, JAI Press, Greenwich (CT), 1995, vol. 1, p. 173; and references cited therein.
18. H.-J. Knölker, M. Bauermeister and J.-B. Pannek, Chem. Ber., 1992, 125, 2783.
19. H.-J. Knölker and W. Fröhner, Tetrahedron Lett., 1997, 38, 4051.
20. H.-J. Knölker, E. Baum and T. Hopfmann, Tetrahedron Lett., 1995, 36, 5339.
21. H.-J. Knölker and W. Fröhner, Tetrahedron Lett., 1996, 37, 9183.
22. H.-J. Knölker and G. Schlechtingen, J. Chem. Soc., Perkin Trans. 1, 1997, 349.
23. H.-J. Knölker and K. R. Reddy, Tetrahedron Lett., 1998, 39, 4007.
24. H.-J. Knölker, M. Bauermeister, J.-B. Pannek and M. Wolpert, Synthesis, 1995, 397.
25. H.-J. Knölker, F. Budei, J.-B. Pannek and G. Schlechtingen, Synlett, 1996, 587.
26. H.-J. Knölker and T. Hopfmann, Synlett, 1995, 981.
27. H.-J. Knölker and M. Wolpert, Tetrahedron Lett., 1997, 38, 533.
28. H.-J. Knölker and W. Fröhner, Synlett, 1997, 1108.
29. H.-J. Knölker and W. Fröhner, Tetrahedron Lett., 1998, 39, 2537.
30. H.-J. Knölker and W. Fröhner, Tetrahedron Lett., 1997, 38, 1535.
31. H.-J. Knölker, W. Fröhner and A. Wagner, Tetrahedron Lett., 1998, 39, 2947.
32. H.-J. Knölker and K. Hartmann, Synlett, 1991, 428.
33. H.-J. Knölker, G. Baum and M. Kosub, Synlett, 1994, 1012.
34. E. Weiss, R. Merényi and W. Hübel, Chem. Ber., 1962, 95, 1170.
35. H.-J. Knölker, J. Heber and C. H. Mahler, Synlett, 1992, 1002.
36. A. J. Pearson, R. J. Shively and R. A. Dubbert, Organometallics, 1992, 11, 4096.
37. H.-J. Knölker and J. Heber, Synlett, 1993, 924.
38. H.-J. Knölker, J. Prakt. Chem., 1994, 336, 277.
39. A. J. Pearson and R. J. Shively, Organometallics, 1994, 13, 578.
40. H.-J. Knölker, E. Baum and J. Heber, Tetrahedron Lett., 1995, 36, 7647.