Difluorocyclopentenone synthesis

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 4025-4029

  Harrington, Paul E ^a   Li, Lianhai ^a   Tius, Marcus A ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE DERIVATIVE; DIFLUOROCYCLOPENTENONE; TRIFLUOROETHANOL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; GEOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033612201     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9900477     Document Type: Article

References (49)

1. Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683.
2. However, see: Snegirev, V. F.; Makarov, K. N. Izv. Akad. Nauk SSR, Ser. Khim. 1986, 1331-1340.
3. (a) Stavber, S.; Zupan, M. Tetrahedron Lett. 1996, 37, 3591-3594.
4. (b) Davis, F. A.; Han, W.; Murphy, C. K. J. Org. Chem. 1995, 60, 4730-4737.
5. (c) Xu, Z.-Q.; DesMarteau, D. D.; Gotoh, Y. J. Fluorine Chem. 1992, 58, 71-79.
6. (d) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, R. G. J. Chem. Soc., Chem. Commun. 1992, 595-596.
7. (e) Differding, E.; Ofner, H. Synlett 1991, 187-189.
8. (a) Tius, M. A.; Kawakami, J. K. Synth. Commun. 1992, 22, 1461-1471.
9. (b) Tius, M. A.; Kawakami, J. K. Synlett 1993, 207-208.
10. (c) Tius, M. A.; Kawakami, J. K. Tetrahedron 1995, 51, 3997-4010.
11. (a) Tius, M. A.; Astrab, D. P.; Fauq, A. H.; Ousset, J.-B.; Trehan, S. J. Am. Chem. Soc. 1986, 108, 3438-3442.
12. (b) Tius, M. A.; Drake, D. J. Tetrahedron 1996, 52, 14651-14860.
13. For example, see: Biggadike, K.; Borthwick, A. D. J. Chem. Soc., Chem. Commun. 1990, 1380-1382.
14. (a) Crowley, P. J.; Howarth, J. A.; Owton, W. M.; Percy, J. M.; Stansfield, K. Tetrahedron Lett. 1998, 37, 5975-5978.
15. (b) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1996, 51, 10289-10302.
16. (c) Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201-9216.
17. (d) Lee, J.; Tsukazaki, M.; Snieckus, V. Tetrahedron Lett. 1993, 34, 415-418.
18. (e) Bennett, A. J.; Percy, J. M.; Rock, M. H. Synlett 1992, 483-484.
19. (f) Patel, S. T.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1992, 1477-1478.
20. (g) Percy, J. M. Tetrahedron Lett. 1990, 31, 3931-3932.
21. (h) Tanaka, K.; Nakai, T.; Ishikawa, N. Tetrahedron Lett. 1978, 19, 4809-4810.
22. (i) Nakai, T.; Tanaka, K.; Ishikawa, N. Chem. Lett. 1976, 1263-1266.
23. (j) Metcalf, B. W.; Jarvi, E. T.; Burkhart, J. P. Tetrahedron Lett. 1985, 26, 2861-2864.
24. (k) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644.
25. (l) Burdon, J.; Coe, P. L.; Haslock, I. B.; Powell, R. L. J. Chem. Soc., Chem. Commun. 1996, 49-50.
26. (m) Burdon, J.; Coe, P. L.; Haslock, I. B.; Powell, R. L. J. Fluorine Chem. 1997, 85, 151-153.
27. Excellent discussions of the Nazarov reaction can be found in the following articles: (a) Habermas, K. L.; Denmark, S. E.; Jones, T. K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1994; Vol. 45, pp 1-158. (b) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 751-784. (c) Denmark, S. E.; Habermas, K. L.; Hite, G. A. Helv. Chim. Acta 1988, 71, 168-194.
28. Excellent discussions of the Nazarov reaction can be found in the following articles: (a) Habermas, K. L.; Denmark, S. E.; Jones, T. K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1994; Vol. 45, pp 1-158. (b) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 751-784. (c) Denmark, S. E.; Habermas, K. L.; Hite, G. A. Helv. Chim. Acta 1988, 71, 168-194.
29. Excellent discussions of the Nazarov reaction can be found in the following articles: (a) Habermas, K. L.; Denmark, S. E.; Jones, T. K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1994; Vol. 45, pp 1-158. (b) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 751-784. (c) Denmark, S. E.; Habermas, K. L.; Hite, G. A. Helv. Chim. Acta 1988, 71, 168-194.
30. (a) Drakesmith, F. G.; Richardson, R. D.; Stewart, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 286-291.
31. (b) Normant, J. F.; Foulon, J. P.; Masure, D.; Sauvêtre, R.; Villieras, J. Synthesis 1975, 122-125.
32. (c) Masure, D.; Sauvêtre, R.; Normant, J. F.; Villieras, J. Synthesis 1976, 761-764.
33. Fish, P. V.; Johnson, W. S.; Jones, G. S.; Tham, F. S.; Kullnig, R. K. J. Org. Chem. 1994, 59, 6150-6152 and references cited.
34. (a) Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
35. (b) Ichikawa, J.; Fujiwara, M.; Okauchi, T.; Minami, T. Synlett 1998, 927-929.
36. Gairaud, C. B.; Lappin, G. R. J. Org. Chem. 1953, 18, 1-3.
37. 2.
38. Hydrolytically labile vinylogous silyl ester 2g was prepared from the hydroxymethylene derivative by treatment with tert-butyldimethylsilyl chloride and triethylamine and was allowed to react with an excess of 1 directly, without isolation. See: Tius, M. A.; Kannangara, G. S. K. Org. Synth. 1993, 71, 158-166.
39. Aldehyde 10 was isolated as a single geometrical isomer of undetermined stereochemistry.
40. β-Chloroenones were prepared according to: Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1976, 41, 636-643.
41. Tius, M. A.; Busch-Petersen, J.; Yamashita, M. Tetrahedron Lett. 1998, 39, 4219-4222.
42. Martin, R.; Romea, P.; Tey, C.; Urpi, F.; Vilarassa, J. Synlett 1997, 1414-1416.
43. We considered using acid chlorides instead of morpholino amides; however, all attempts to add the (simple) Gilman cuprate derived from 1 to α-methyl-trans-cinnamoyl chloride led to very complicated reaction mixtures.
44. 4)/NMO.
45. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276.
46. 2.
47. Ichikawa, J.; Kobayashi, M.; Yokota, N.; Noda, Y.; Minami, T. Tetrahedron 1994, 50, 11637-11646.
48. (a) Jones, T. K.; Denmark, S. E. Helv. Chim. Acta 1983, 66, 2377-2396.
49. (b) Jones, T. K.; Denmark, S. E. Helv. Chim. Acta 1983, 66, 2397-2411.