Studies on the transition metal-catalyzed synthesis of variously substituted (E)-3-[1-(aryl)methylidene]- and (E)-3-(1-alkylidene)-3H-furan-2-ones

Tetrahedron

Volumn 54, Issue 1-2, 1998, Pages 135-156

  Rossi, Renzo ^a   Bellina, Fabio ^a   Bechini, Chiara ^a   Mannina, Luisa ^b   Vergamini, Piergiorgio ^a  

^a UNIVERSITY OF PISA   (Italy)

^b University of Mouse   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FURANONE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0031986190     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10265-4     Document Type: Article

References (52)

1. 1. For leading references on Ag-catalyzed intramolecular additions of carboxylic acids to alkynes, see:(a) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871-772;
2. (b) Kotora, M.; Negishi, E. Synthesis 1997, 121-128;
3. (c) Jong, T-T.; Williard, P. G.; Porwell, J. P. J. Org. Chem. 1984, 49, 735-736;
4. (d) Pale, P.; Chuche, J. Tetrahedron Lett. 1987, 28, 6447-6448;
5. (e) Kotora, M.; Negishi, E. Tetrahedron 1997, 53, 6707-6738.
6. 2. For leading references on Hg-catalyzed intramolecular additions of carboxylic acids to alkynes, see: (a) Jellal, A.; Grimaldi, J.; Santelli, M. Tetrahedron Lett. 1984, 25, 3179-3182;
7. (b) Yamamoto, M. J. Chem. Soc. Perkin Trans I 1981, 582-587;
8. (c) Krafft, G. A.; Katznellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459-5466;
9. (d) Amos., R. A.; Katznellebogen, J. A. J. Org. Chem. 1978, 43, 560-564;
10. (d) Spencer, R. W.; Tam, T. F.; Thomas, E.; Robinson, V. J.; Krantz, A. J. Am. Chem. Soc. 1986, 108, 5589-5597;
11. (e) Ref. 1e.
12. 3. For leading references on Rh-catalyzed intramolecular additions of carboxylic acids to alkynes, see: (a) Marder, T. B.; Chan, D. M.-T.; Fultz, W. C.; Calabrese, J. C.; Milstein, D. J. Chem. Soc. Chem. Commun. 1987, 1865-1867;
13. (b) Chan, D. M.-T.; Marder, T. B.; Milstein, D.; Taylor, N. J. Am. Chem. Soc. 1987, 109, 6385-6388;
14. (c) Ref 1e.
15. 4. For leading references on Pd-catalyzed intramolecular additions of carboxylic acids to alkynes, see: (a) Ref 1b;
16. (b) Kotora, M.; Negishi, E. Tetrahedron Lett. 1996, 37, 9041-9042;
17. (c) Lambert, C.; Utimoto, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 5323-5326;
18. (d) Ref. 1e.
19. 5. Yanagihara, N.; Lambert, C.; Iritani, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 2753-2754.
20. 6. Boussy, D.; Goré, J.; Balme, G. Tetrahedron Lett. 1992, 33, 2811-2814.
21. 7. Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976-982.
22. 8. (a) Cavicchioli, M.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron Lett. 1996, 37, 1429-1432;
23. (b) Cavicchioli, M.; Decortat, S.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron 1996, 52, 11463-11478.
24. 9. Lu, X.; Huang, X.; Ma, S. Tetrahedron Lett. 1993, 34, 5963-5966.
25. 10. Kundu, N. G.; Pal, M. J. Chem. Soc. Chem. Commun. 1993, 86-88.
26. 12. Huang, Y.; Alper, H. J. Org. Chem. 1991, 56, 4534-4536.
27. 13. For leading references, see: (a) Rao, Y. S. Chem. Rev. 1976, 76, 625-694;
28. (b) Rao, Y. S. Chem. Rev. 1964, 64, 353-388;
29. (c) Abdalla, M.; Essawy, A. Indian J. Chem. Sect. B 1977, 15B, 523-525.
30. 14. (a) Rossi, R.; Bellina, F.; Carpita, A. Synlett 1996, 356-358;
31. (b) Rossi, R. Bellina, F.; Mannina, L. Tetrahedron 1997, 53, 1025-1044;
32. (c) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis, in press;
33. (d) Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R. Tetrahedron 1994, 50, 12029-12046.
34. 15. For examples of 5-aryl-2(3H)-furanones with antifungal activity, see: Sakurai, K.; Matsumoto, H.; Adachi, J. Yakugaku Zasshi 1968, 88, 919-924; Chem. Abstr. 1968, 69, 94792i.
35. 15. For examples of 5-aryl-2(3H)-furanones with antifungal activity, see: Sakurai, K.; Matsumoto, H.; Adachi, J. Yakugaku Zasshi 1968, 88, 919-924; Chem. Abstr. 1968, 69, 94792i.
36. 16. For examples of (E)-3-[1-(aryl)methylidene]-tetrahydrofuran-2-ones with antifungal activity, see: (a) Ref 15;
37. (b) Wamhoff, H.; Matolcsy, G. Z. Natuforsch. 1969, 24B, 651-652.
38. 17. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470;
39. (b) Rossi, R.; Carpita, A,; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 127-160.
40. 18. (a) Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Gazz. Chim. Ital. 1995, 125, 381-392;
41. (b) Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R. Tetrahedron Lett. 1994, 35, 6913-6916.
42. 19. For a review on selective transition metal-catalyzed cross-coupling reactions which involve polyhalogenated ethene derivatives, see: Rossi, R.; Bellina, F. Org. Prep. Proc. Int. 1997, 29, 137-176.
43. 20. Herrmann, W. A.; Brossner, C.; Öfele, K.; Reisinger, C-P.; Priemieier, T.; Beller, M.; Fischer, H. Angew.. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
44. 3N, see: Hegedus, L.; Weider, P. S.; Mulhern, T. A.; Asada, H.; D'Andrea, S. Gazz. Chim. Ital. 1986, 116, 213-219, and references cited therein.
45. 22. For the oxidative addition of carboxylic acids to Pd(0) complexes, see: Trost, M.; Romzero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268-4278.
46. 23. Coulson, D. R. Inorg. Synth. 1972, 13, 121-124.
47. 24. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
48. 25. Doyle, J. R.; Slade, P.E.; Jonassen, M. B. Inorg. Synth. 1960, 6, 216-219.
49. 26. Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press, London, 1985, p. 17.
50. 27. Dérien, S.; Clinet, J. C.; Duñach, E.; Périchon, J. J. Org. Chem. 1993, 58, 2578-2588.
51. 28. Bélanger, A.; Brassard, P. Can. J. Chem. 1975, 53, 195-200.
52. 29. Schuler, F. W.; Hanna, C. J. Am. Chem. Soc. 1951, 73, 3528-3530.