Palladium(0)-catalyzed allylation of 2,2′-dihydroxybiphenyl by 1-ethenylcyclopropyl sulfonates: Preparation of 2,2′-bis(cyclopropylideneethoxy) biphenyls

Synthesis

Volumn , Issue 15, 2002, Pages 2271-2279

  Delogu, Giovanna ^a   Salaün, Jacques ^b   De Candia, Cristina ^a,b   Fabbri, Davide ^a,b   Piras, Pier Paolo ^c   Ollivier, Jean ^b  

^a CNR   (Italy)

^b UNIVERSITÉ PARIS SUD   (France)

^c Sez Microbiologia   (Italy)

Author keywords

1 ethenylcyclopropyl sulfonates; Allylation; Biphenyls; Palladium(0); Rearrangements

Indexed keywords

CATALYSIS; ESTERS; PALLADIUM;

ALLYLATION;

SYNTHESIS (CHEMICAL);

BIPHENYL DERIVATIVE; PALLADIUM; POTASSIUM SALT; PROPANOL; SULFONIC ACID DERIVATIVE;

ALLYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0036412426     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34950     Document Type: Article

References (59)

1. (a) Tanaka, T.; Kouno, I. J. Nat. Prod. 1996, 59, 997.
2. (b) Li, H.-Y.; Nehira, T.; Hagiwara, M.; Harada, N. J. Org. Chem. 1997, 62, 7222.
3. (c) Charlton, J. L. J. Nat. Prod. 1998, 61, 1448.
4. (d) Glombitza, K.-W.; Schmidt, A. J. Nat. Prod. 1999, 62, 1238.
5. (e) Bringmann, G.; Breuningm, M.; Tasler, S. Synthesis 1999, 525.
6. (a) Uchida, I.; Shigematsu, N.; Ezaki, M.; Hashimoto, M.; Aoki, H.; Imanaka, I. J. Antibiot. 1985, 38, 1462.
7. (b) Fujihashi, T.; Hara, H.; Sakata, T.; Mori, K.; Higuchi, H.; Tanaka, A.; Kaji, H.; Kaji, A. Antimicrob. Agents Chemother.
8. (c) Nicolaou, K. C.; Boddy, C. N.; Bräse, S.; Wissinger, N. Angew. Chem. Int. Ed. 1999, 38, 2096.
9. (d) Baumeinster, B.; Sakai, N.; Gerard, D.; Matile, S. Angew. Chem. Int. Ed. 2000, 39, 1955.
10. (e) Itoh, T.; Shirakami, S.; Ishida, N.; Yamashita, Y.; Yoshida, T.; Kim, H.-S.; Wataya, Y. Bioorg. Med. Chem. Lett. 2000, 20, 1657.
11. (f) Tohma, H.; Morioka, H.; Takizawa, S.; Arisawa, M.; Kita, Y. Tetraahedron 2001, 57, 345.
12. (g) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331.
13. (h) For a review on conformationally flexible biphenyls and their uses in stoichiometric and catalytic processes see: Delogu, G.; Vallee, Y. In Recent Research and Developments in Organic Chemistry; Pandalai, S. G., Ed.; Transworld Research: India, 2002, 1-39.
14. (a) Brady, J. D.; Sadler, I. H.; Fry, S. C. Phytochemistry 1998, 47, 349.
15. (b) Song, Q.; Fronczek, F. R.; Fischer, N. H. Phytochemistry 2000, 55, 653.
16. (c) Tene, M.; Wabo, H. K.; Hamnaing, P.; Tsopmo, A.; Tane, P.; Ayafor, J. F.; Sterner, O. Phytochemistry 2000, 54, 975.
17. (a) Mazaleyra, J.-P.; Gaucher, A.; Avrda, J.; Wakselman, M. Tetrahedron: Asymmetry 1997, 8, 619.
18. (b) Gaucher, A.; Bintein, F.; Wakselamn, M.; Mazaleyrat, J.-P. Tetrahedron Lett. 1998, 39, 575.
19. (c) Brandmeier, V.; Feigel, M.; Bremer, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 486.
20. (a) Salaün, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987, Chap. 13, 809-878.
21. (b) In Houben-Weyl, Methods of Organic Chemistry, Vol. E17a-f; de Meijere, A., Ed.; Thieme: Stuttgart, 1997.
22. (c) Salaün, J. Top. Curr. Chem. 1988, 144, 1.
23. (a) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
24. (b) Salaün, J. Top. Curr. Chem. 2000, 207, 1.
25. Shizuri, Y.; Yamada, K. Phytochemistry, 1985, 24, 1385.
26. (a) Henick, C. A.; Willy, W. E.; Staal, G. B.; Ludvik, G. F. J. Agric. Food Chem. 1976, 24, 1023.
27. (b) Janiak, S. CIBA Ltd., Ger., Offen. 1911520, 1968 CA 72: 21484n.
28. Wright, S. W.; Harris, R. R.; Kerr, J. S.; Green, A. M.; Pinto, D. J.; Bruin, E. M.; Collins, R. J.; Dorow, R. L.; Montegna, L. R.; Sherk, S. R.; Covington, M. B.; Nurnberg, S. A.; Welch, P. K.; Nelson, M. J.; Magolda, R. L. J. Med. Chem. 1992, 35, 4961.
29. Blanc, M.; Tamir, A.; Aubriot, S.; Michel, M. C.; Bouzoubaa, M.; Leclerc, G.; Demerge, P. J. Med. Chem. 1998, 41, 1613.
30. (a) Stolle, A.; Ollivier, J.; Piras, P. P.; Salaün, J.; de Meijere, A. J. Am. Chem. Soc. 1992, 114, 4051.
31. (b) Ollivier, J.; Dorizon, P.; Piras, P. P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37.
32. (c) Salaün, J. Russ. J. Org. Chem. 1997, 33, 742
33. (d) Ollivier, J.; Girard, N.; Salaün, J. Synlett 1999, 1539.
34. (e) Paschetta, V.; Cordero, F. M.; Paugam, R.; Ollivier, J.; Brandi, A.; Salaün, J. Synlett 2001, 1233.
35. (a) Chevtchouk, T.; Ollivier, J.; Salaün, J. Tetrahedron: Asymmetry 1997, 8, 1005.
36. (b) Chevtchouk, T.; Ollivier, J.; Salaün, J. Tetrahedron: Asymmetry 1997, 8, 1011.
37. (c) Stolle, A.; Becker, H.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1994, 35, 3517.
38. (d) Stolle, A.; Becker, H.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1994, 35, 3521.
39. (e) Atlan, V.; Racouchot, S.; Rubin, M.; Bremer, C.; Ollivier, J.; de Meijere, A.; Salaün, J. Tetrahedron: Asymmetry 1998, 9, 1131.
40. (f) Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J.; Cordero, F. M.; Goti, A.; Brandi, A. J. Org. Chem. 1997, 62, 8276.
41. (g) Ferrara, M.; Cordero, F. M.; Goti, A.; Brandi, A.; Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J. Chem. -Eur. J. 1999, 2725.
42. (h) Pisaneschi, F.; Cordero, F. M.; Goti, A.; Paugam, R.; Ollivier, J.; Brandi, A.; Salaün, J. Tetrahedron: Asymmetry 2000, 11, 897.
43. (i) Cordero, F. M.; Pisaneschi, F.; Goti, A.; Ollivier, J.; Salaün, J.; Brandi, A. J. Am. Chem. Soc. 2000, 122, 8075.
44. For reviews see: (a) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (b) Goti, A.; Cordero, F. M.; Brandi, A. Top. Curr. Chem. 1996, 178, 1.
45. For reviews see: (a) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (b) Goti, A.; Cordero, F. M.; Brandi, A. Top. Curr. Chem. 1996, 178, 1.
46. Salaün, J. Chem. Rev. 1983, 83, 619.
47. Salaün, J. Chem. Rev. 1989, 89, 1247.
48. Sylvestre, I.; Ollivier, J.; Salaün, J. Tetrahedron Lett. 2001, 42, 4991.
49. (a) Delogu, G.; Fabbri, D. Tetrahedron: Asymmetry 1997, 8, 759.
50. (b) Delogu, G.; Fabbri, D.; Dettori, M. A. Tetrahedron: Asymmetry 1998, 9, 2819.
51. Suarez, M.; Bonilla, J.; de Diaz, A. M. P.; Achenbach, H. Phytochemistry 1983, 22, 609; and references cited therein.
52. Ogata, M.; Hoshi, M.; Urano, S.; Endo, T. Chem. Pharm. Bull. 2000, 48, 1467; and references cited therein.
53. Fujita, S.; Taira, J. Free Radical Biol. Med. 1994, 17, 273; and references cited therein.
54. Taira, T.; Takeschi Iketmoto, T.; Yoneya, T.; Hagi, A.; Murakami, A.; Makino, K. Free Radical Res. Commun. 1992, 6, 197; and references cited therein.
55. (a) Frater, G.; Schmid, H. Helv. Chim. Acta 1970, 53, 269.
56. (b) Falshaw, C. P.; Lane, S. A.; Ollis, W. D. J. Chem. Soc., Chem. Commun. 1973, 491.
57. Delogu, G.; Fabbri, D.; Dettori, M. A.; Casalone, G.; Forni, A. Tetrahedron: Asymmetry 2000, 11, 1827.
58. (a) Frater, G.; Schmid, H. Helv. Chim. Acta 1970, 53, 269.
59. (b) Falshaw, C. P.; Lane, S. A.; Ollis, W. D. J. Chem. Soc., Chem. Commun. 1973, 491.