Chiral (E,E)-1,4-dialkoxy-1,3-butadienes. 1. Stereoselective synthesis

Tetrahedron Letters

Volumn 38, Issue 39, 1997, Pages 6921-6924

  Virgili, Marina ^a   Moyano, Albert ^a   Pericàs, Miquel A ^a   Riera, Antoni ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 1,4 DIALKOXY 1,3 BUTADIENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DECOMPOSITION; DIMERIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0030819880     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01622-5     Document Type: Article

References (24)

1. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; John Wiley, New York: 1990.
2. Meister, H. Chem. Ber. 1963, 96, 1688.
3. Symmetrical 1,4-dialkoxy-1,3-butadienes: (a) Scheeren, J. W.; Marcelis, A. T. M.; Aben, R. W.; Nivard, R. J. F. Recl. Trav. Chim. Pays-Bas 1975, 94, 196.
4. (b) Keana, J. F. W.; Eckler, P. E. J. Org. Chem. 1976, 41, 2625.
5. (c) Kirmse, W.; Scheidt, F.; Vater, H.-J. J. Am. Chem. Soc. 1978, 100, 3945.
6. (d) Boeckman, R. K., Jr.; Dolak, T. M.; Culos, K. O. J. Am. Chem. Soc. 1978, 100, 7098.
7. (e) van Rijn, P.; Everhardus, R. H.; van der Ven, J.; Brandsma, L. Recl. Trav. Chim. Pays-Bas 1981, 100, 372.
8. (f) Hiranuma, H.; Miller, S. I. J. Org. Chem. 1982, 47, 5083.
9. (g) Hiranuma, H.; Miller, S. I. J. Org. Chem. 1983, 48, 3096.
10. Unsymmetrical 1,4-dialkoxy-1,3-butadienes: (a) David, S.; Eustache, J. J. Chem. Soc., Perkin Trans. 1 1979, 2230.
11. (b) Maddaluno, J.; Gaonac'h, O.; Le Gallic, Y.; Duhamel, L. Tetrahedron Lett. 1995, 36, 8591.
12. (c) Guillam, A.; Maddaluno, J.; Duhamel, L. Chem. Commun. 1996, 1295.
13. Valentí, E.; Pericàs, M. A.; Serratosa, F. J. Am. Chem. Soc. 1990, 112, 7405.
14. Moyano, A.; Charbonnier, F.; Greene, A. E. J. Org. Chem. 1987, 52, 2919.
15. Solà, L.; Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1992, 33, 2863.
16. Negishi, E.; Van Horn, D. E. J. Am. Chem. Soc. 1977, 99, 3168.
17. Yoshifuji, M.; Loots, M. J.; Schwartz, J. Tetrahedron Lett. 1977, 18, 1303.
18. 2: C, 79.50; H, 11.68). (NOTE: Due to the high sensitivity of the dialkoxydiene, the reaction glassware was washed with aqueous NaOH and oven-dried prior to use).
19. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
20. These chiral alcohols are either commercially available or can be obtained according to published literature procedures. b: Schwartz, A.; Madan, P.; Whitesell, J. K.; Lawrence, R. M. Org. Synth. 1990, 69, 1.
21. c: Ort, O. Org. Synth. 1987, 62, 203.
22. d: Oppolzer, W.; Chapuis, C.; Dao, G. M.; Reichlin, D.; Godel, T. Tetrahedron Lett. 1982, 23, 4781.
23. e: Oppolzer, W.; Chapuis, C.; Dupuis, D.; Guo, H. Helv. Chim. Acta 1985, 68, 2100.
24. f: Oghikawa, T.; Yamashita, M. Bull. Chem. Soc. Jpn. 1989, 62, 3177.