Cycloisomerization of enynes catalyzed by iron(0)-ate complexes

Journal of the American Chemical Society

Volumn 127, Issue 35, 2005, Pages 12236-12237

  Fürstner, Alois ^a   Martin, Rubén ^a   Majima, Keisuke ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE; IRON COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CLUSTER ANALYSIS; COMPLEX FORMATION; CYCLIZATION; ISOMERIZATION; REACTION ANALYSIS;

EID: 24644523532     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0532739     Document Type: Article

References (41)

1. (a) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
2. (b) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609.
3. (a) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2003, 42, 308.
4. (b) Fürstner, A.; Méndez, M. Angew. Chem., Int. Ed. 2003, 42, 5355.
5. (c) Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943.
6. (d) Seidel, G.; Laurich, D.; Fürstner, A. J. Org. Chem. 2004, 69, 3950.
7. (e) Scheiper, B.; Glorius, F.; Leitner, A.; Fürstner, A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11960.
8. (f) Fürstner, A.; De Souza, D.; Parra-Rapado, L.; Jensen, J. T. Angew. Chem., Int. Ed. 2003, 42, 5358.
9. (g) Lepage, O.; Kattnig, E.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 15970.
10. (h) Fürstner, A.; Turet, L. Angew. Chem., Int. Ed. 2005, 44, 3462.
11. Reviews: (a) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
12. (b) Fürstner, A.; Martin, R. Chem. Lett. 2005, 624.
13. General review on organoiron chemistry: Semmelhack, M. F. In Organometallics in Synthesis. A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, U.K., 2002; p 1003.
14. (a) Jonas, K.; Schieferstein, L. Angew. Chem., Int. Ed. Engl. 1979, 18, 549.
15. (b) Jonas, K.; Schieferstein, L.; Krüger, C.; Tsay, Y.-H. Angew. Chem., Int. Ed. Engl. 1979, 18, 550.
16. (c) Jonas, K.; Klusmann, P.; Goddard, R. Z. Naturforsch., B: Chem. Sci. 1995, 50, 394.
17. (d) Jonas, K.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1980, 19, 520.
18. Martin, R.; FUrstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955.
19. For related work, see: (a) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura E. J. Am. Chem. Soc. 2004, 126, 3686.
20. (b) Nagano, T.; Hayashi T. Org. Lett. 2004, 6, 1297.
21. (c) Bedford, R. B.; Bruce, D. W.; Frost, R. M.; Goodby, J. W.; Hird, M. Chem. Commun. 2004, 2822.
22. Reviews: (a) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674.
23. (b) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525.
24. It should be mentioned that the available mechanistic information does not allow us to rule alternative mechanisms out. Notably, the formation of allyliron species (by allylic C-H activation) instead of the putative metallacyclic intermediates could also explain the observed results.
25. For ene-type reactions of ene/diene substrates using iron catalysts formed in situ, see: (a) Takacs, J. M.; Newsome, P. W.; Kuehn, C.; Takusagawa, F. Tetrahedron 1990, 46, 5507.
26. (b) Takacs, J. M.; Anderson, L. G. J. Am. Chem. Soc. 1987, 109, 2200.
27. Low-valent titanium: (a) Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
28. (b) Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511.
29. Authoritative reviews: (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
30. (b) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
31. (c) Trost, B. M.; Krische, M. J. Synlett 1998, 1.
32. (d) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215.
33. (e) Fairlamb, I. J. S. Angew. Chem., Int. Ed. 2004, 43, 1048.
34. Leading references: (a) [Ru]: Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2002, 124, 5025.
35. (b) [Pd]: Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
36. (c) [Pd]: Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 49, 249.
37. (d) [Rh]: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198 and literature cited therein.
38. Review: Ellis, J. E. Adv. Organomet. Chem. 1990, 31, 1.
39. For the assignment of the stereochemistry, cf. Supporting Information.
40. Precedence for the stereochemical switch from cis to trans on going to larger ring sizes is found in organopalladium chemistry, cf: Trost, B. M.; Grese, T. A. J. Am. Chem. Soc. 1991, 113, 7363.
41. GC investigations show that the E-isomer does not result from equilibration but is the primary product of the reaction.