[5+1] Cocyclization of (cyclopropylmethylene)cyclopropanes and other vinylcyclopropanes with carbon monoxide catalyzed by octacarbonyldicobalt

Synlett

Volumn , Issue 17, 2005, Pages 2619-2622

  Kurahashi, Takuya ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Cobalt; Cycloaddition; Transition metals

Indexed keywords

1 VINYLSPIROPENTANE; 1,1 DIVINYLCYCLOPROPANE; CARBENE; CARBON MONOXIDE; CARBONYL DERIVATIVE; COBALT DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYLMETHYLENE; DICYCLOPROPYL(CYCLOPROPYLIDENE)METHANE; ISOPROPENYLCYCLOPROPANE; METHANE; OCTACARBONYLDICOBALT; PENTANE; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG; VINYLCYCLOPROPANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; STOICHIOMETRY;

EID: 27444437034     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917102     Document Type: Article

References (46)

1. (a) Part 120 in the series 'Cyclopropyl Building Blocks for Organic Synthesis'. For Part 119 see: Dalai, S.; Limbach, M.; Zhao, L.; Tamm, M.; Sevvana, M.; de Meijere, A. Synthesis 2005, in press.
2. (b) For Part 118 see: Yucel, B.; Arve, L.; de Meijere, A. Tetrahedron 2005, in press.
3. Oppolzer, W. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991, 315.
4. For a comprehensive review on the stoichiometric Pauson-Khand reaction see: Schore, N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991, 1037.
5. For recent reviews on the Pauson-Khand reaction see: (a) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32.
6. (b) Gibson, S. E.; Stevenazzi, A. Angew. Chem. Int. Ed. 2003, 42, 1800;
7. Angew. Chem. 2003, 115, 1844.
8. (c) Rivero, M. R.; Adrio, J.; Carretero, J. C. Eur. J. Org. Chem. 2002, 2881.
9. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263.
10. [5+1] Cocyclizations of vinylcyclopropanes: (a) Ben-Shoshan, R.; Sarel, S. J. Chem. Soc., Chem. Commun. 1969, 883.
11. (b) Victor, R.; Ben-Shoshan, R.; Sarel, S. Tetrahedron Lett. 1970, 11, 4253.
12. (c) Sarel, S. Acc. Chem. Res. 1978, 11, 204.
13. (d) Aumann, R. J. Am. Chem. Soc. 1974, 96, 2631.
14. (e) Taber, D. F.; Kanai, K.; Jiang, Q.; Bui, G. J. Am. Chem. Soc. 2000, 122, 6807.
15. (f) Taber, D. F.; Joshi, P. V.; Kanai, K. J. Org. Chem. 2004, 69, 2268.
16. [5+1] Cocyclizations with cyclopropene derivatives: (g) Grabowski, N. A.; Hughes, R. P.; Jaynes, B. S.; Rheingold, A. L. J. Chem. Soc., Chem. Commun. 1986, 1694.
17. (h) Cho, S. H.; Liebeskind, L. S. J. Org. Chem. 1987, 52, 2631.
18. (i) Semmelhack, M. F.; Ho, S.; Steigerwald, M.; Lee, M. C. J. Am. Chem. Soc. 1987, 109, 4397.
19. [5+1] Cocyclizations of allenylcyclopropanes: (j) Iwasawa, N.; Owada, Y.; Matsuo, T. Chem. Lett. 1995, 115.
20. (k) Owada, Y.; Matsuo, T.; Iwasawa, N. Tetrahedron 1997, 53, 11069.
21. Iridium-catalyzed [5+1] cycloadditions of allenylcyclopropanes: (l) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4.
22. Ruthenium-catalyzed [5+1] cocyclizations of cyclopropyl ketimines: (m) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230.
23. Wiberg, K. B.; Ellison, G. B.; Wendoloski, J. J.; Brundle, C. R.; Kuebler, N. A. J. Am. Chem. Soc. 1976, 98, 7179.
24. (a) Carbocyclic Three-Membered Ring Compounds, In Methods of Organic Chemistry (Houben-Weyl), Vol. E17a-c; de Meijere, A., Ed.; Thieme: Stuttgart, 1996.
25. (b) Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
26. For a stable methylenecyclopropanecobalt complex see: Förster, J.; Kozhushkov, S. I.; Binger, P.; Wedemann, P.; Noltemeyer, M.; de Meijere, A.; Butenschön, H. Chem. Commun. 1998, 239.
27. For cobalt-mediated Pauson-Khand reactions involving methylenecyclopropanes see: de Meijere, A.; Becker, H.; Stolle, A.; Kozhushkov, S. I.; Bes, M. T.; Salaün, J.; Noltemeyer, M. Chem. Eur. J. 2005, 11, 2471; and references cited therein.
28. A cobalt complex-catalyzed [3+1] cocyclization of CO and methylenecyclopropanes without a vinyl substituent involving a cobaltacyclopropane intermediate has also been observed. See: Kurahashi, T.; de Meijere, A. Angew. Chem. Int. Ed. 2005, in press.
29. For cyclopropylmethylmetal to homoallylmetal rearrangements concerning other transition metals see: (a) de Meijere, A.; Nüske, H.; Es-Sayed, M.; Labahn, T.; Schroen, M.; Bräse, S. Angew. Chem. Int. Ed. 1999, 38, 3669;
30. Angew. Chem. 1999, 111, 3881.
31. (b) Nüske, H.; Noltemeyer, M.; de Meijere, A. Angew. Chem. Int. Ed. 2001, 40, 3411;
32. Angew. Chem. 2001, 113, 3509.
33. (c) Larock, R. C.; Varaprath, S. J. Org. Chem. 1984, 49, 3432.
34. (d) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379.
35. (e) Wender, P. A.; Williams, T. J. Angew. Chem. Int. Ed. 2002, 41, 4550;
36. Angew. Chem. 2002, 114, 4732.
37. (f) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203.
38. (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977.
39. (b) Billington, D. C.; Kerr, W. J.; Pauson, P. L.; Farnocchi, C. F. J. Organomet. Chem. 1988, 356, 213.
40. (c) Rautenstrauch, V.; Mégard, P.; Conesa, J.; Küster, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 1413;
41. Angew. Chem. 1990, 102, 1441.
42. (d) Jeong, N.; Hwang, S. H.; Lee, Y. S.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
43. (e) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y. S.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793.
44. (f) Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
45. (g) Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
46. 12O (136.2): C, 79.37; H, 8.88. Found: C, 79.22; H, 8.76.