(E)-N-Isopropyl-5-tosyl-4-pentenamide: A vinyl sulfone as precursor of a new δ-acyldienyl anion equivalent

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2833-2836

  Caturla, Francisco ^a   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343183018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00399-1     Document Type: Article

References (19)

1. (a) Werstiuk, N. H. Tetrahedron 1983, 39, 205-268.
2. (b) Stowell, J. C. Chem. Rev. 1984, 84, 409-435.
3. (c) Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932-948.
4. (d) Werstiuk, N. H. In Umpoled Synthons; Hase, T. A., Ed.; John Wiley & Sons: New York, 1987; pp 173-216.
5. (e) Nájera, C.; Yus, M. Trends in Organic Chemistry 1991, 2, 155-181.
6. (a) Bonete, P.; Nájera, C. Tetrahedron Lett. 1992, 33, 4065-4068.
7. (b) Bonete, P.; Nájera, C. J. Org. Chem. 1994, 59, 3202-3209.
8. Bonete, P.; Nájera, C. Tetrahedron 1995, 51, 2763-2776 and references cited therein.
9. The use of (2E,4E)-5-tosyl-2,4-pentadienamides as δ-acyldienyl cation equivalents have been recently described: Bernabeu, M. C.; Chinchilla, R.; Naδjera, C. Tetrahedron Lett. 1995, 36, 3901-3904.
10. For instance, dienamideś and esters are common flavour constituents and show physiological and insecticidal activities.
11. They have been postulated as intermediates: Mandai, T.; Moriyama, T.; Tsujimoto, K.; Kawada, M.; Otera, J. Tetrahedron Lett. 1986, 27, 603-606.
12. (a) Nájera, C.; Baldó, B.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1988, 1029-1032.
13. (b) Nájera, C.; Sansano, J. M.; Yus, M. J. Chem. Educ. 1995, 664-665.
14. For lithiated vinyl sulfones see: Ibañez, P. L.; Nájera, C. Tetrahedron Lett. 1993, 34, 2003-2006 and references cited therein.
15. Purchased from Aldrich.
16. The dilithiation of acid 7a with n-BuLi took place at the vinyl position to give the expected dianion which reacted with propanal to give the corresponding tosyl substituted hydroxyacid; however, the isomerization and dehydrosulfinylation under basic conditions failed.
17. Miyashita, M.; Yoshihoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772-3774.
18. The deuterium incorporation was determined by mass spectrometry.
19. For intramolecular Michael addition of amides to vinyl sulfones see: Li, C.; Fuchs, P. L. Synlett 1994, 629-630 and references cited therein.