New transformations from a 3-silyloxy 2-aza-1,3-diene: Consecutive Zr- mediated retro-Brook rearrangement and reactions with electrophiles

Tetrahedron

Volumn 56, Issue 26, 2000, Pages 4467-4472

  Gandon, Vincent ^a   Bertus, Philippe ^a   Szymoniak, Jan ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Azadiene; Electrophilic addition; Retro Brook; Zirconium

Indexed keywords

ALKADIENE;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034705377     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00310-0     Document Type: Article

References (39)

1. (a) Boger, D. L. Comprehensive Organic Synthesis, Vol. 5, Trost, B. M., Fleming, I., Eds. Pergamon, Oxford, 1991, p 451.
2. (b) Ghosez, L.; Bayard, P.; Nshimyumukiza, P.; Gouverneur, V.; Sainte, F.; Beaudegnies, R.; Rivera, M.; Frisque-Hesbain, A.-M.; Wynants, C. Tetrahedron 1995, 51, 11021.
3. (c) Barluenga, J.; Joglar, J.; González, F. J.; Fustero, S. Synlett 1990, 129.
4. (d) Gouverneur, V.; Ghosez, L. Tetrahedron 1996, 52, 7585.
5. (e) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387.
6. (f) Jnoff, E.; Ghosez, L. J. Am. Chem. Soc. 1999, 121, 2617.
7. Boger D.L., Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis. 1987;Academic, London.
8. (a) Bandini, E.; Martelli, G.; Spunta, G.; Panunzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1999, 10, 1445.
9. (b) Bongini, A.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. J. Org. Chem. 1997, 62, 8911.
10. (c) Barluenga, J.; Carlón, R. P.; Peláez, E.; Joglar, J.; Ortiz, F. L. Tetrahedron 1992, 48, 9745.
11. (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Dev. 1998, 2, 49.
12. (b) Lasarte, J.; Palomo, C.; Picard, J. P.; Dunogues, J.; Aizpurua, J. M. J. Chem. Soc., Chem. Commun. 1989, 72.
13. (a) Wender, P. A.; Schaus, J. M. J. Org. Chem. 1978, 43, 782.
14. (b) Martin, S. F.; Phillips, G. W.; Puckette, T. A.; Colapret, J. A. J. Am. Chem. Soc. 1980, 102, 5866.
15. (a) Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 4469.
16. (b) Buchwald, S. L.; Watson, B. T.; Wannamaker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486.
17. (c) Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1989, 111, 4495.
18. Gandon V., Bertus P., Szymoniak J. Tetrahedron Lett. 41:2000;3053.
19. 2Zr' chemistry, see: (a) Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn 1998, 71, 755.
20. (b) Negishi, E.; Kondakov, D. Y. Chem. Soc. Rev. 1996, 26, 417.
21. (c) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124.
22. (d) Negishi, E. Chem. Scripta 1989, 29, 457.
23. Scholz J., Kahlert S., Görls H. Organometallics. 17:1998;2876.
24. A retro-[1,4]-Brook rearrangement (C4-Si bond forming process) exclusively occurred starting from the more crowded 1,4-diphenyl-3-trimethylsilyloxy-2-aza-1,3-butadiene. In this case, similar structural environment at C1 and C4 in the substrate led to the generally easier Zr-C bond-breaking.
25. (a) Panek, J. S. Comprehensive Organic Synthesis, Vol. 1, Trost, B. M., Fleming, I., Eds.; Pergamon, Oxford, 1991, p. 580.
26. (b) Colvin, E. W. Silicon in Organic Synthesis, Krieger, R. E. Publishing Company, Malabar, FL, 1985.
27. Meyers, A. I.; Mihelich, E. D. Angew. Chem. 1976, 88, 321; Angew. Chem., Int. Ed. Engl. 1976, 15, 270.
28. Meyers, A. I.; Mihelich, E. D. Angew. Chem. 1976, 88, 321; Angew. Chem., Int. Ed. Engl. 1976, 15, 270.
29. This feature corroborates the total regioselectivity of the Meyers C-alkylation of 2-oxazolines, see Ref. 12.
30. 2O or by treatment with KF in MeOH, see Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 881.
31. We have proved the complex to be quite inert towards insertion of carbonyl compounds and even isocyanides into the Zr-C bond.
32. Werner R.M., Barwick M., Davis J.T. Tetrahedron Lett. 36:1995;7395.
33. Ager D.J. Synthesis. 1984;384.
34. Lithiated 2-silylmethyl-1,3-oxazines have been demonstrated to react efficiently with aldehydes, see Sachdev, K. Tetrahedron Lett. 1976, 4041.
35. To elaborate the 1,3-diene system via the Peterson reaction, the reactions of α-silylallylanions with saturated aldehydes are generally employed.
36. Chan T.H., Chang E., Vinokur E. Tetrahedron Lett. 1970;1137.
37. Kazuyoshi T., Kanoko T., Hiroaki T., Rie S., Masumi T., Haruo O. Chem. Pharm. Bull. 37:1989;2334.
38. Casadei M.A., Cesa S., Inesi A., Franco M. J. Chem. Res. 5:1995;1064.
39. Garcia M.J., Rebolledo F., Gotor V. Tetrahedron. 50:1994;6935.