Studies on the reactivity of methyl γ-tosylcrotonoate as ambident reagent in organic synthesis

Tetrahedron

Volumn 52, Issue 48, 1996, Pages 15243-15256

  Caturla, Francisco ^a   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYRIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030602245     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00929-5     Document Type: Article

References (26)

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15. 6. Caturla, F.; Nájera, C. Tetrahedron Lett. 1996, 37, 4787-4790.
16. 7. Other bases such as LDA, BunLi, BusLi, or ButLi at -78°C gave decomposition of the starting sulfone 4.
17. 8. For NMR studies about endo/exo and s-cis/s-trans structures of dienolate of crotonic acid see: (a) Aurell, M. J.; Gil, S.; Mestres, R.; Parra, M.; Tortajada, A. Tetrahedron 1994, 50, 5109-5118.
18. (b) Domingo, L. R.; Gil, S.; Mestres, R.; Picher, M. T. Tetrahedron 1995, 51, 7207-7214.
19. 9. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477-3478.
20. 10. The same results were obtained in the reduction of γ-alkylated products derived from amide 2.6
21. 11. Trost, B. M.; Merlic, C. A. J. Org. Chem. 1990, 55, 1127-1129.
22. 12. 4-(Phenylsulfonyl)butanoic acid dianion has been widely used in organic synthesis; see, for instance: Kiddle, J. J.; Green, D. L. C.; Thompson, C. M. Tetrahedron 1995, 51, 2851-2864 and references cited therein.
23. 13. O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663-2666.
24. 14. Mixture of products.
25. 15. Very complicated spectrum; carbon signals could not be assigned.
26. 16. The stereochemistry could not be assigned (see text).