Palladium-catalyzed synthesis of 2E-[(methoxycarbonyl)methylene]tetrahydrofurans: Oxidative cyclization-methoxycarbonylation of 4-yn-1-ols versus cycloisomerization-hydromethoxylation

Journal of Organometallic Chemistry

Volumn 593-594, Issue , 2000, Pages 409-415

  Gabriele, Bartolo ^a   Salerno, Giuseppe ^a   De Pascali, Francesca ^a   Costa, Mirco ^b   Chiusoli, Gian Paolo ^b  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

2 Methoxy 2 methyltetrahydrofurans; 2E (Methoxycarbonyl)methylene tetrahydrofurans; 4 Yn 1 ols; Carbonylation; Palladium

Indexed keywords

EID: 0034649930     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00492-1     Document Type: Article

References (34)

1. Bonardi A., Costa M., Gabriele B., Salerno G., Chiusoli G.P. Tetrahedron Lett. 36:1995;7495.
2. Bacchi A., Chiusoli G.P., Costa M., Sani C., Gabriele B., Salerno G. J. Organomet. Chem. 562:1998;35.
3. (a) B. Gabriele, G. Salerno, F. De Pascali, G. Tomasi Scianò, M. Costa, G.P. Chiusoli, Tetrahedron Lett. 38 (1997) 6877.
4. (b) B. Gabriele, G. Salerno, F. De Pascali, M. Costa, G.P. Chiusoli, J. Org. Chem. 64 (1999) 7687.
5. (a) A. Bacchi, G.P. Chiusoli, M. Costa, B. Gabriele, C. Righi, G. Salerno, Chem. Commun. (1997) 1209.
6. (b) G.P. Chiusoli, M. Costa, B. Gabriele, G. Salerno, J. Mol. Catal. A 143 (1999) 297.
7. See, for example (a) B. Muckensturm, D. Pflieger, J. Chem. Res. S (1986) 376.
8. (b) B. Muckensturm, D. Pflieger, J. Chem. Res. M (1986) 3265.
9. (a) T.A. Bryson, J. Org. Chem. 38 (1973) 3428.
10. (b) S.A. Krueger, T.A. Bryson, J. Org. Chem. 39 (1974) 3167.
11. (c) W.P. Jackson, S.V. Ley, J.A. Morton, J. Chem. Soc. Chem. Commun. (1980) 1028.
12. (d) M.T. Reetz, Angew. Chem. Int. Ed. Engl. 93 (1981) 716.
13. (e) S. Ohta, A. Shimabayashi, S. Hayakawa, M. Sumino, M. Okamoto, Synthesis (1985) 45.
14. (f) G. Sauve, P. Delongchamps, Synth. Commun. 15 (1985) 201.
15. (g) M. Yamaguchi, I. Hirao, Chem. Lett. (1985) 337.
16. (h) P.H. Lambert, M. Vaultier, R. Carrie, J. Org. Chem. 50 (1985) 5352.
17. (i) J.P. Michael, G.D. Hosken, A.S. Howard, Tetrahedron 44 (1988) 3025.
18. (j) D. Pflieger, B. Muckensturm, Tetrahedron 45 (1989) 2031.
19. (k) M. Sato, J. Sakaki, Y. Sugita, S. Yasuda, H. Sakoda, C. Kaneko, Tetrahedron 47 (1991) 5689.
20. (l) J. Sakaki, Y. Sugita, M. Sato, C. Kaneko, Tetrahedron 47 (1991) 6197.
21. (m) T.R. Hoye, K.B. Crawford, J. Org. Chem. 59 (1994) 520.
22. 2/KI-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols to give furan derivatives has been reported recently: (a) B. Gabriele, G. Salerno, Chem. Commun. (1997) 1083.
23. (b) B. Gabriele, G. Salerno, E. Lauria, J. Org. Chem. 64 (1999) 7693.
24. P.G. Sammes, D.J. Weller, Synthesis (1995) 1205 and references cited therein.
25. Gabriele B., Costa M., Salerno G., Chiusoli G.P. J. Chem. Soc. Perkin Trans. 1:1993;83.
26. Gabriele B., Salerno G., De Pascali F., Costa M., Chiusoli G.P. J. Chem. Soc. Perkin Trans. 1:1997;147.
27. Tsuji J. Palladium Reagents and Catalysts. 1995;Wiley, New York.
28. 2-catalysed exo-dig cyclization of internal 4-yn-1-ols in aqueous acetonitrile to give 1-hydroxy-4-ones as well as the formation of spiroacetals from 3-yn-1,7-diols, 3-yn-1,8-diols and 4-yn-1,9-diols has been reported: K. Utimoto, Pure Appl. Chem. 55 (1983) 1845. More recently, the Pd(II)-catalyzed cyclization of 5-silyl-substituted 4-yn-1-ols to give 2,3-dihydrofurans has been reported: S. Schabbert, E. Schaumann, Eur. J. Org. Chem. (1998) 1873.
29. (a) G. Cologne, Bull. Soc. Chim. Fr. (1954) 799.
30. (b) J. Flahaut, P. Miginiac, Helv. Chim. Acta 61 (1978) 2275.
31. (c) F.E. McDonald, J.L. Bowman, Tetrahedron Lett. 37 (1996) 4675.
32. Smith A.B., Malamas M.S. J. Org. Chem. 47:1982;3442.
33. Swadesh S., Smith S., Dunlop A.D. J. Org. Chem. 16:1951;476.
34. G. Eglinton, E.R.H. Jones, M.C. Whiting, J. Chem. Soc. (1952) 2873.