Conjugated elimination versus [1,2]-Wittig rearrangement of unsaturated diox(ol)anes

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 373-377

  Lemiègre, Loïc ^a   Regnier, Thomas ^a   Combret, Jean Claude ^b   Maddaluno, Jacques ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ACETAL DERIVATIVE; ACRYLIC ACID; ALKADIENE; DIOXANE DERIVATIVE; HETEROCYCLIC COMPOUND; ISOPRENE; LITHIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COMPETITIVE BEHAVIOR; KINETICS; MOLECULAR STABILITY; PROTON TRANSPORT; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE; THERMODYNAMICS; WITTIG REARRANGEMENT;

EID: 0037421065     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02568-6     Document Type: Article

References (36)

1. Recent examples: (a) Tomooka, K.; Yamamoto, H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4500; (b) Tomooka, K.; Kikuchi, M.; Igawa, K.; Suzuki, M.; Keong, P.-H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4502; (c) Katritzky, A. R.; Fang, Y. Heterocycles 2000, 53, 1783; (d) Kitagawa, O.; Momose, S.-I.; Yamada, Y.; Shiro, M.; Taguchi, T. Tetrahedron Lett. 2001, 42, 4865; (e) Barluenga, J.; Fananas, F. J.; Sanz, R.; Marcos, C.; Trabada, M. Org. Lett. 2002, 4, 1587.
2. Recent examples: (a) Tomooka, K.; Yamamoto, H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4500; (b) Tomooka, K.; Kikuchi, M.; Igawa, K.; Suzuki, M.; Keong, P.-H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4502; (c) Katritzky, A. R.; Fang, Y. Heterocycles 2000, 53, 1783; (d) Kitagawa, O.; Momose, S.-I.; Yamada, Y.; Shiro, M.; Taguchi, T. Tetrahedron Lett. 2001, 42, 4865; (e) Barluenga, J.; Fananas, F. J.; Sanz, R.; Marcos, C.; Trabada, M. Org. Lett. 2002, 4, 1587.
3. Recent examples: (a) Tomooka, K.; Yamamoto, H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4500; (b) Tomooka, K.; Kikuchi, M.; Igawa, K.; Suzuki, M.; Keong, P.-H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4502; (c) Katritzky, A. R.; Fang, Y. Heterocycles 2000, 53, 1783; (d) Kitagawa, O.; Momose, S.-I.; Yamada, Y.; Shiro, M.; Taguchi, T. Tetrahedron Lett. 2001, 42, 4865; (e) Barluenga, J.; Fananas, F. J.; Sanz, R.; Marcos, C.; Trabada, M. Org. Lett. 2002, 4, 1587.
4. Recent examples: (a) Tomooka, K.; Yamamoto, H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4500; (b) Tomooka, K.; Kikuchi, M.; Igawa, K.; Suzuki, M.; Keong, P.-H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4502; (c) Katritzky, A. R.; Fang, Y. Heterocycles 2000, 53, 1783; (d) Kitagawa, O.; Momose, S.-I.; Yamada, Y.; Shiro, M.; Taguchi, T. Tetrahedron Lett. 2001, 42, 4865; (e) Barluenga, J.; Fananas, F. J.; Sanz, R.; Marcos, C.; Trabada, M. Org. Lett. 2002, 4, 1587.
5. Recent examples: (a) Tomooka, K.; Yamamoto, H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4500; (b) Tomooka, K.; Kikuchi, M.; Igawa, K.; Suzuki, M.; Keong, P.-H.; Nakai, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 4502; (c) Katritzky, A. R.; Fang, Y. Heterocycles 2000, 53, 1783; (d) Kitagawa, O.; Momose, S.-I.; Yamada, Y.; Shiro, M.; Taguchi, T. Tetrahedron Lett. 2001, 42, 4865; (e) Barluenga, J.; Fananas, F. J.; Sanz, R.; Marcos, C.; Trabada, M. Org. Lett. 2002, 4, 1587.
6. Inter alia: (a) Antoniotti, P.; Tonacchini, G. J. Org. Chem. 1998, 63, 9756; (b) Jursic, B. S. Int. J. Quantum Chem. 1999, 73, 299; (c) Sheldon, J. C.; Taylor, M. S.; Bowie, J. H.; Dua, S.; Chia, C. S. B.; Eichinger, P. C. H. J. Chem. Soc., Perkin Trans. 2 1999, 333.
7. Inter alia: (a) Antoniotti, P.; Tonacchini, G. J. Org. Chem. 1998, 63, 9756; (b) Jursic, B. S. Int. J. Quantum Chem. 1999, 73, 299; (c) Sheldon, J. C.; Taylor, M. S.; Bowie, J. H.; Dua, S.; Chia, C. S. B.; Eichinger, P. C. H. J. Chem. Soc., Perkin Trans. 2 1999, 333.
8. Inter alia: (a) Antoniotti, P.; Tonacchini, G. J. Org. Chem. 1998, 63, 9756; (b) Jursic, B. S. Int. J. Quantum Chem. 1999, 73, 299; (c) Sheldon, J. C.; Taylor, M. S.; Bowie, J. H.; Dua, S.; Chia, C. S. B.; Eichinger, P. C. H. J. Chem. Soc., Perkin Trans. 2 1999, 333.
9. Recent contributions in the field: (a) Maleczka, R. E.; Geng, F. J. Am. Chem. Soc. 1998, 120, 8551; (b) Tomooka, K.; Yamamoto, K.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1999, 38, 3741.
10. Recent contributions in the field: (a) Maleczka, R. E.; Geng, F. J. Am. Chem. Soc. 1998, 120, 8551; (b) Tomooka, K.; Yamamoto, K.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1999, 38, 3741.
11. Tomooka K., Yamamoto H., Nakai T. J. Am. Chem. Soc. 118:1996;3317.
12. Tomooka K., Kikuchi M., Igawa K., Keong P.-H., Nakai T. Tetrahedron Lett. 40:1999;1917.
13. Gärtner P., Letschnig M.F., Knollmüller M., Völlenkle H. Tetrahedron: Asymmetry. 10:1999;4811.
14. Gärtner P., Letschnig M.F., Knollmüller M., Mereiter K. Tetrahedron: Asymmetry. 11:2000;1003.
15. Gaonac'h O., Maddaluno J., Chauvin J., Duhamel L. J. Org. Chem. 56:1991;4045.
16. Maddaluno J., Gaonac'h O., Le Gallic Y., Duhamel L. Tetrahedron Lett. 36:1995;8591.
17. Martin C., Maddaluno J., Duhamel L. Tetrahedron Lett. 37:1996;8169.
18. Deagostino A.M., Maddaluno J., Mella M., Prandi C., Venturello P. J. Chem. Soc., Perkin Trans. 1. 1998;881.
19. Guillam A., Toupet L., Maddaluno J. J. Org. Chem. 63:1998;5110.
20. Guillam A., Toupet L., Maddaluno J. J. Org. Chem. 64:1999;9348.
21. A comparable concept relying on protected diols has been put forward recently by Maleczka and Geng (Ref. 3a).
22. (a) Deagostino, A.; Balma Tivola, P.; Prandi, C.; Venturello, P. Synthesis 1999, 1841. Experimental details are given in: (b) Bataille, C.; Bégin, G.; Guillam, A.; Lemiègre, L.; Lys, C.; Maddaluno, J.; Toupet, L. J. Org. Chem., in press.
23. (a) Deagostino, A.; Balma Tivola, P.; Prandi, C.; Venturello, P. Synthesis 1999, 1841. Experimental details are given in: (b) Bataille, C.; Bégin, G.; Guillam, A.; Lemiègre, L.; Lys, C.; Maddaluno, J.; Toupet, L. J. Org. Chem., in press.
24. For another access to these compounds see Ref 6a.
25. A [1,2]-Wittig/β-elimination competition, as well as a temperature effect is reported by Gärtner et al. (Ref. 5b).
26. No [2,3]-Wittig rearrangement was observed on acetals 8 by contrast with similar unsaturated aminals that yield significant amounts of the corresponding products: Blanchard, N.; Mangeney, P., unpublished results.
27. Details on the conditions providing ester 11, a useful triene for intramolecular Diels-Alder reactions, are described in Lemiègre, L. Ph.D. Thesis, Université de Rouen, 2002 and will be published later on.
28. Caballero M., Garcia-Valverde M., Pedrosa R., Vicente M. Tetrahedron: Asymmetry. 7:1996;219.
29. Ballini R., Bosica G., Cossu S., De Lucchi O., Peluso P. Tetrahedron. 57:2001;4461.
30. Collum D.B. Acc. Chem. Res. 25:1992;448.
31. Naito K., Rickborn B. J. Org. Chem. 45:1980;4061.
32. Moss R.J., Rickborn B. J. Org. Chem. 49:1984;3694.
33. Mioskowski C., Manna S., Falck J.R. Tetrahedron Lett. 25:1984;519.
34. Fujiwara S., Katsumura S., Isoe S. Tetrahedron Lett. 31:1990;691.
35. Venturello P. J. Chem. Soc., Chem. Commun. 1992;1032.
36. Deagostino A., Prandi C., Venturello P. Tetrahedron. 52:1996;1433.