Reaction of 3-trimethylsilyloxy-2-aza-1,3-dienes with zirconocene: A transition metal promoted retro-Brook rearrangement

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3053-3056

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

^a Université de Reims Champage Ardenne   (France)

Author keywords

Aza compounds; Brook; Rearrangements; Zirconium and compounds

Indexed keywords

AMIDE; HETEROCYCLIC COMPOUND; ZIRCONIUM; ZIRCONOCENE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HYDROLYSIS; NONHUMAN; REACTION ANALYSIS; SYNTHESIS;

EID: 0034701570     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00333-6     Document Type: Article

References (26)

1. (a) Ntirampebura, D.; Ghosez, L. Tetrahedron Lett. 1999, 4, 7079 and references cited therein
2. (b) Bongini, A.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. J. Org. Chem. 1997, 62, 8911
3. (c) Ghosez, L.; Bayard, P.; Nshimyumukiza, P.; Gouverneur, V.; Sainte, F.; Beaudegnies, R.; Rivera, M.; Frisque-Hesbain, A.-M.; Wynants, C. Tetrahedron 1995, 51, 11021
4. (d) Barluenga, J.; Carlón, R. P.; Peláez, E.; Joglar, J.; Ortiz, F. L. Tetrahedron 1992, 48, 9745
5. (e) Barluenga, J.; Joglar, J.; González, F. J.; Fustero, S. Synlett 1990, 129.
6. For the generation of metalloenamines by the reduction of 2-azadienes with lithium reagents, see: Martin, S. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p. 475.
7. (a) Scholz, J.; Kahlert, S.; Görls, H. Organometallics 1998, 17, 2876
8. (b) Davis, J. M.; Whitby, R. J.; Jaxa-Chamiec, A. J. Chem. Soc., Chem. Commun. 1991, 1743.
9. (a) Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 4469
10. (b) Buchwald, S. L.; Watson, B. T.; Wannamaker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486
11. (c) Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1989, 111, 4495.
12. Bertus, P.; Gandon, V.; Szymoniak, J. J. Chem. Soc., Chem. Commun. 2000, 171.
13. (a) The electronically neutral 1-phenyl-2-aza-1,3-pentadiene does not react with zirconocene. This lack of reactivity may be related to a generally low HOMO activity of the neutral 2-azadienes, see Ref. 1
14. (b) for the preparation of silyloxy azadienes 1, 4 and 6, see Ref. 1c.
15. 2Zr' chemistry, see: (a) Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755
16. 2Zr' chemistry, see: (b) Negishi, E.; Kondakov, D. Y. Chem. Soc. Rev. 1996, 26, 417
17. 2Zr' chemistry, see: (c) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124
18. 2Zr' chemistry, see: (d) Negishi, E. Chem. Scr. 1989, 29, 457.
19. (a) Compound 3 was converted to 2 by treatment with 3 M HCl
20. 23NOSi: 297.1549.
21. (a) Comanita, B. M.; Woo, S.; Fallis, A. G. Tetrahedron Lett. 1999, 40, 5283
22. (b) Bailey, W. F.; Jiang, X.-L. Organometallics 1995, 14, 5704
23. (c) He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905
24. (d) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213.
25. At a lower temperature (-80°C) the singlet of the Cp ligands broadened, suggesting the presence of two diastereotopic Cp units. The fluxionality of the complex may be related to the dynamic behavior of zirconocene complexes with 1-aza- and 1,4-diazadienes, see Ref. 3.
26. 2Zr', see Refs. 3 and 4.