Tandem [2 + 2] cycloaddition-cycloreversion reactions in highly polar media: A convergent one-pot entry to substituted alkenes and dienes

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7143-7146

  Arrastia, Iosune ^a   Cossío, Fernando P ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030599223     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01562-6     Document Type: Article

References (28)

1. 1. Wittig, G. Angew. Chem., Int. Ed. Engl. 1962, 1 , 415.
2. 2. Peterson, D. J. J. Org. Chem. 1968, 33 , 781.
3. 3. For excellent reviews see: (a) Tidwell, T.T. Ketenes; Wiley: New York, 1995; pp. 564-571.
4. (b) Pommier, A.; Pons, J. M. Synthesis . 1993, 441.
5. See also: (c) Danhaiser, R. L.; Nowick, J. S. J. Org. Chem . 1991, 56 , 1176.
6. (d) Danhaiser, R. L.; Choi, Y. M.; Menichincheri, M.; Stoner, E. J. J. Org. Chem . 1993, 53 , 322.
7. 4. Ojima, J.; Itagawa, K.; Hamai, S.; Nakada, T.; Kuroda, S. J. Chem. Soc., Perkin Trans. 1983, 2997.
8. 5. (a) Neidlein, R.; Bernhard, E. Angew. Chem., Int. Ed. Engl. 1978, 17 , 369.
9. (b) Moore, H. W.; Mercer, F.; Kunert, D.; Albaugh, P. J. Am. Chem. Soc . 1979, 101 , 5434.
10. 6. (a) Lecea, B.; Arrieta, A.; Roa, G.; Ugalde, J. M.; Cossío, F. P. J. Am. Chem. Soc . 1994, 116 , 9613.
11. (b) Lecea, B.; Arrieta, A.; López, X.; Ugalde, J. M.; Cossío, F. P. J. Am. Chem. Soc . 1995, 117, 12314.
12. 7. Moyano, A.; Pericàs, M. A.; Valentí, E. J. Org. Chem . 1989, 54 , 573.
13. 8. Mulzer, J.; Zippel, M.; Brüntrup, G. Angew. Chem., Int. Ed. Engl. 1980, 19 , 465.
14. 9. Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc . 1990, 112 , 4595.
15. 10. Waldmann, H. Angew. Chem., Int. Ed. Engl . 1991, 30 , 1306.
16. 5 for 4 h prior to use. We have found that this treatment is essential for a succesful experiment.
17. 6, reflux) to yield [4+2] cycloadducts. See Brady, W. T.; Agno, M. O. J. Org. Chem . 1983, 48 , 5337.
18. 13. This process has been postulated by Mulzer and can be schematized as follows: (Equation Presented)
19. See for example: (a) Mulzer, J.; Kerkmann, T. J. Am. Chem. Soc . 1980, 102 , 3620.
20. (b) Mulzer, J.; Zippel, M. Angew. Chem., Int. Ed. Engl . 1981, 20 , 399.
21. 14. (a) Jubault, P.; Feasson, C.; Collignon, N. Bull. Soc. Chim. Fr. 1994, 131 , 1101.
22. (b) Villieràs, J.; Perriot, P.; Normant, J.F. Synthesis . 1975, 458.
23. 15. (a) Krijnen, E. S.; Zuilhof, H.; Lodder, G. J. Org. Chem. 1994, 59 , 8139.
24. 16. Handbook of Chemistry and Physics; CRC Press: Ohio, 1976-77; p C-250.
25. 17. (a) Crombie, L.; Crombie, W. M. L. J. Chem. Soc., Perkin Trans. 1, 1994, 1267.
26. (b) Elvidge, J.A.; Jones, J. R.; Mane, R.B.; Saljoughian, M. J. Chem. Soc., Perkin Trans. 1, 1978, 1191.
27. (c) Concepcion, A. B.; Maruoka, K.; Yamamoto, H. Tetrahedron . 1995, 51, 4011.
28. (d) Saljoughian, M.; Williams, P. G. J. Org. Chem . 1987, 52, 3481.