Palladium-Mediated Cyclization on Carbohydrate Templates. 1. Synthesis of Enantiopure Bicyclic Compounds

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1341-1347

  Nguefack, Jean Flaubert ^a   Bolitt, Véronique ^a   Sinou, Denis ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001022232     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961881o     Document Type: Article

References (52)

1. (a) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
2. (b) Heumann, A.; Regnier, M. Tetrahedron 1995, 51, 975.
3. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 23, 1173.
4. (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
5. (e) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
6. (f) Oppolzer, W. Pure Appl. Chem. 1988, 60, 39.
7. (g) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631.
8. (h) Tsuji, J. Palladium Reagents and Catalysts; Innovations in Organic Synthesis; Wiley: Chichester, 1995.
9. Oppolzer, W. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46.
10. (j) Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365.
11. (k) Hegedus, L. S. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994; p 383.
12. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valey, 1994.
13. Tietze, L. F. Chem. Ind. (London) 1995, 453.
14. (n) Malacria, M. Chem. Rev. 1996, 96, 289.
15. (o) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813.
16. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
17. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715 and 779.
18. (c) Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron 1990, 46, 1385.
19. (d) Curran, D. P. Synthesis 1988, 417 and 489.
20. (e) Ramaiah, M. Tetrahedron 1987, 43, 3541.
21. (f) Jasperse, C. P.; Curran, D. P., Fevig, T. L. Chem. Rev. 1991, 91, 1237.
22. (g) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1332.
23. (a) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
24. (b) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369.
25. (a) Engelbrecht, G. J.; Holzapfel, C. W. Tetrahedron Lett. 1991, 32, 2161.
26. (b) Holzapfel, C. W.; van der Merwe, T. L. Tetrahedron Lett. 1996, 37, 2303 and 2307.
27. (a) Lindsell, W. E.; Preston, P. N.; Rettie, A. B. Carbohydr. Res. 1994, 254, 311.
28. (b) Marco-Contelles, J. Tetrahedron Lett. 1994, 35, 5059.
29. (c) Naz, N.; Al-Tel, T. H.; Al-Abed, Y.; Voelter, W. Tetrahedron Lett. 1994, 35, 8581.
30. (d) Naz, N.; Al-Tel, T. H.; Al-Abed, Y.; Voelter, W.; Ficker, R.; Hiller, W. J. Org. Chem. 1996, 61, 3250.
31. Trost, B. M.; Sevanne, P.; Mignani, S.; Acemogen, M. J. Am. Chem. Soc. 1989, 111, 7487.
32. Nguefack, J.-F; Bolitt, V.; Sinou, D. J. Chem. Soc., Chem. Commun. 1995, 1893.
33. Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 570.
34. Frappa, I.; Sinou, D. Synth. Commun. 1995, 25, 2941.
35. Saïah, M.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1992, 33, 4317.
36. Baer, H. H.; Hanna, Z. S. Can. J. Chem. 1981, 59, 889.
37. Grynkiewicz, G. Carbohydr. Res. 1984, 128, C9.
38. Chatterjee, S; Negishi, E.-I. J. Org. Chem. 1985, 50, 3406.
39. Jeffery, T. Tetrahedron Lett. 1993, 34, 1133.
40. Bernocchi, E.; Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1992, 33, 3073.
41. (a) Hacksell, U.; Daves, G. D., Jr. Organometallics 1983, 2, 772.
42. (b) Francis, J. W.; Henry, P. M. Organometallics 1992, 11, 2832.
43. (c) Saito, S.; Kara, T.; Takahashi, N.; Hirai, M.; Moriwake, T. Synlett 1992, 237.
44. (d) Hosokawa, T.; Sagafuji, T.; Yamanaka, T.; Murahashi, S. I. J. Organomet. Chem. 1994, 470, 253.
45. (e) Ma, S.; Lu, X. J. Organomet. Chem. 1993, 447, 305.
46. (f) Kimura, M.; Harayama, H.; Tanaka, S.; Tamaru, Y. J. Chem. Soc., Chem. Commun. 1994, 2531.
47. (a) Duanet, J. P.; Cheng, C. H. Tetrahedron Lett. 1993, 34, 4019.
48. (b) Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
49. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
50. Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. Tetrahedron 1985, 41, 375.
51. Bussas, R.; Kresze, G. Liebigs Ann. Chem. 1980, 629.
52. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 2033.