(E)-5-Tosyl-4-pentenamide: A vinyl sulfone for the one-pot general synthesis of indolizidine derivatives

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3789-3792

  Caturla, Francisco ^a   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343632380     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00736-3     Document Type: Article

References (19)

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2. (b) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
3. For last reviews on this topic see: (a) Michael, J. P. Nat. Prod. Rep. 1995, 12, 535-552.
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6. For recent syntheses using sulfones see for instance: (a) Sheehan, S. M., Padwa, A. J. Org. Chem. 1997, 62, 438-439.
7. (b) Carretero, J. C.; Gómez Arrayás, R. J. Org. Chem. 1995, 60, 6000-6001.
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12. Caturla, F.; Nájera, C. Tetrahedron Lett. 1996, 37, 2833-2836.
13. For a recent synthesis using 4-pentenamide as starting material see: Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802-4809.
14. For other intramolecular Michael addition of amides to vinyl sulfones see: Li, C.; Fuchs, P. L. Synlett 1994, 629-630 and references cited therein.
15. Molecular Mechanics calculations (Hyperchem 5 from Hypercube) and Altona (developed by Cerdá-Garcia-Rojas, C. M.; Gerardo, L. and Joseph-Nathan, P.) showed also torsion angles and coupling constants for the more stable conformation in agreement with the observed coupling constants.
16. Trost, B. M., Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477-3478.
17. Substituted 4-pentenoic acids are accesible by Claisen-Ireland rearrangement.
18. See reference 3b.
19. We are very grateful to the DGICYT, Spain (Project no. PB94-1515) for financial support.