Stereoselective [4 + 1] annulation reactions with silyl vinylketenes derived from fischer carbene complexes

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6542-6546

  Moser, William H ^a   Feltes, Laura A ^a   Sun, Liangdong ^a   Giese, Matthew W ^a   Farrell, Ryan W ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; FISCHER-TROPSCH SYNTHESIS; HYDROCARBONS; OLEFINS; REACTION KINETICS;

ANNULATION REACTIONS; CARBENOID REAGENTS; CYCLOPENTENONE PRODUCTS; SILYL VINYLKETENES;

STEREOCHEMISTRY;

ALKYNE DERIVATIVE; CARBENOID; CYCLOPENTENONE DERIVATIVE; DIAZOMETHANE; KETONE DERIVATIVE; REAGENT; SILANE DERIVATIVE; VINYL DERIVATIVE;

ANNULATION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; CYCLOADDITION; ISOMERIZATION; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 33747397917     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060994x     Document Type: Article

References (42)

1. For reviews, see: (a) Gibson, S. E.; Lewis, S. E.; Mainolfi, N. J. Organomet. Chem. 2004, 689, 3873.
2. (b) Tius, M. A. Acc. Chem. Res. 2003, 36, 284.
3. (c) Mitsudo, T.; Kondo, T. Synlett 2001, 309.
4. (d) Mikolajczyk, M.; Mikina, M.; Zurawinski, R. Pure Appl. Chem. 1999, 71, 473.
5. (e) Iwasawa, N. Synlett 1999, 13.
6. (f) Piancatelli, G.; D'Auria, M.; D'Onofrio, F. Synthesis 1994, 867.
7. (g) Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467.
8. (h) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1.
9. (i) Ramaiah, M. Synthesis 1984, 529.
10. For recent reviews of the Pauson- Khand reaction, see: (a) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem.-Eur. J. 2001, 7, 1589.
11. (b) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263.
12. (c) Keun Chung, Y. Coord. Chem. Rev. 1999, 188, 297.
13. (d) Oliver, G.; Schmalz, H. Angew. Chem., Int. Ed. 1998, 37, 911.
14. (e) Schore, N. E. Org. React. 1991, 40, 1.
15. For a rhodium-catalyzed carbonylative [4 + 1] cycloaddition, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2691.
16. For a review, see: Tidwell, T. T. Ketenes; Wiley: New York, 1991.
17. Vinylketenes stabilized by transition metals have also been utilized as four-carbon synthons. See: Gibson, S. E. Adv. Organomet. Chem. 1999, 44, 275.
18. (a) Davie, C. P.; Danheiser, R. L. Angew. Chem., Int. Ed. 2005, 44, 5867.
19. (b) Rigby, J. H.; Wang, Z. Org. Lett. 2003, 5, 263.
20. (c) Dalton, A. M.; Zhang, Y.; Davie, C. P.; Danheiser, R. L. Org. Lett. 2002, 4, 2465.
21. (d) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Am. Chem. Soc. 1998, 120, 9690.
22. (e) Colomvakos, J. D.; Egle, I.; Ma, J.; Pole, D. L.; Tidwell, T. T.; Warkentin, J. J. Org. Chem. 1996, 61, 9522.
23. Bennett, D. M.; Okamoto, I.; Danheiser, R. L. Org. Lett. 1999, 1, 641.
24. Huang, W.; Tidwell, T. T. Synthesis 2000, 457 and references therein.
25. (a) Pommier, A.; Kocienski, P.; Pons, J. J. Chem. Soc., Perkin Trans. 11998, 2105.
26. (b) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Org. Chem. 1998, 63, 8380.
27. Moser, W. H.; Sun, L.; Huffman, J. C. Org. Lett. 2001, 3, 3389.
28. Dötz, K. H.; Fügen-Köster, B. Chem. Ber. 1980, 113, 1449.
29. See the Supporting Information for X-ray crystallographic structures.
30. Waters, M. L.; Brandvold, T. A.; Isaacs, L.; Wulff, W. D.; Rheingold, A. L. Organometallics 1998, 17, 4298.
31. Silyl vinylketenes 8-11 were also suitable for [4 + 1] annulation reactions. Results with these substrates will be reported elsewhere.
32. Creary, X. In Organic Syntheses; Wiley & Sons: New York, 1990; Collect. Vol. VII, pp 438-443.
33. Moore, H. W.; Yerxa; B. R. Adv. Strain Org. Chem. 1995, 4, 81.
34. Huang, W.; Fang, D.; Temple, K.; Tidwell, T. T. J. Am. Chem. Soc: 1997, 119, 2832.
35. For a review on torquoselective electrocyclic reactions, see: Dolbier, W. R., Jr.; Koroniak, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471.
36. Poland, L. D.; Karlsson, J. O.; Perri, S. T.; Schwabe, R.; Xu, S. L.; Patil, S.; Moore, H. W. J. Am. Chem. Soc. 1989, 111, 975.
37. (a) Tidwell, T. T. Acc. Chem. Res. 1990, 23, 273.
38. (b) Baigne, L. M.; Seikaly, H. R.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 5391.
39. (a) Davies, S. G.; Dohohoe, T. J. Synlett 1993, 323.
40. (b) Davies, S. G.; Donohoe, T. J.; Williams, J. M. J. Pure Appl. Chem. 1992, 64, 379.
41. (c) Uemura, M.; Minami, T.; Hayashi, Y. J. Organomet. Chem. 1986, 299, 119.
42. Similar rate accelerations have been observed for Nazarov cyclizations, which are also proposed to proceed through electrocyclic ring closures of pentadienyl cations. See: Habermas, K. L.; Denmark, S. E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1994; Vol. 45, pp 1-158.