Eu(fod)3 and SnCl4-catalyzed heterocycloadditions of O-silyl enol ethers deriving from cyclic ketones

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8647-8650

  Dujardin, Gilles ^a   Martel, Arnaud ^a   Brown, Eric ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; ETHER DERIVATIVE; EUROPIUM; KETONE DERIVATIVE; SILANE DERIVATIVE; TIN CHLORIDE;

ARTICLE; CATALYSIS; CATALYST; REACTION ANALYSIS;

EID: 0032548054     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01969-8     Document Type: Article

References (24)

1. 1. (a) Boger, D.L. ; Weinreb, S.N. Hetero Diels Alder Methodology in Organic Synthesis ; Academic Press : San Diego, 1987.
2. (b) Waldmann, H. Synthesis 1994, 535-551.
3. (c) Tietze, L.F. ; Kettschau, G. Top. Curr. Chem. 1997, 189. 1-120.
4. (d) Tietze, L.F. ; Kettschau, G. ; Gewert, V.A. ; Schuffenhaner, A. Curr. Org. Chem. 1998, 2, 19-62.
5. (e) Gorman, D.B. ; Tomlinson, I.A. J. Chem. Soc. Chem. Commun. 1998, 25-6.
6. 2. Dujardin, G. ; Rossignol, S. ; Brown, E. Synthesis, 1998, 763-70 and references cited therein.
7. 3. Evans, D.A. ; Johnson, J.S. J. Amer. Chem.Soc., 1998, 120, 4985-6
8. 4. Rousseau, G. Tetrahedron 1995, 51, 2777-849.
9. 13C NMR, elemental analysis and/or MS
10. 7 or reflux for 2d, 90% yield in this case).
11. 7. a) Cazeau, P. ; Moulines, F. ; Laporte, O. ; Duboudin, F. J. Organomet. Chem. 1980, 201-4.
12. b) Duhamel, P. ; Hennequin, L. ; Poirier, J.M. ; Tavel, G. ; Vottero, C. Tetrahedron 1986. 42, 4777-86.
13. 8. (a) Mizukami, S. ; Kihara, N. ; Endo, T. Tetrahedron Lett. 1993, 34, 7437-40;
14. (b) Tietze, L.F. ; Glüsenkamp, K.H. ; Harms, K. ; Remberg, G. ; Sheldrick, G.M. Tetrahedron Lett. 1982, 23, 1147-50;
15. (c) Jones, D.W. ; Lock, C.J.J. Chem. Soc. Chem. Commun. 1991, 1509-10;
16. (d) Sato, M. ; Sunami, S. ; Kaneko, C. ; Satoh, S. ; Furuya, T. Tetrahedron : Asymmetry 1994, 5, 1665-8
17. 9. El-Abed, D. ; Jellal, A. ; Santelli, M. Tetrahedron Lett. 1984, 25, 4503-4.
18. 10. Telan, L.A. ; Poon, C.D. ; Evans, Jr., S.A. J. Org. Chem. 1996, 61, 7455-62.
19. 11 The X-ray crystallographic studies were performed in le Mans by R. Retoux, using a Stoe-Siemens 4-circle diffractometer. Complete crystallographic data will be reported elsewhere.
20. 12. Tietze, L.F. ; Schneider, C. ; Grote, A. Chem. Eur. J. 1996, 139-48 and references cited therein.
21. 13. Sera, A. ; Ueda, N. ; Itoh, K. ; Hiroaki, Y. Heterocycles 1996, 43, 2205-14.
22. 14. Burfeindt, J. ; Patz, M. ; Müller, M. ; Mayr, H. J. Amer. Soc. Chem.Soc. 1998, 120, 3629-34.
23. 3 were reported to be endo directing, the latter leading to an anomalous regioisomeric adduct. See : Arseniyadis, S. ; Rodriguez, R. ; Camara, J. ; Gallard, J.F. ; Guittet, E. ; Toupet, L. ; Ourisson, G. Tetrahedron 1995, 51, 9947-72.
24. 16. Martel, A. ; Dujardin, G. ; Brown, E. Unpublished results.