Dilithiated (E)-N-isobutyl-4-tosyl-2-butenamide: An allyl sulfone dianion for the regiospecific γ-functionalization of crotonamide dianion

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4787-4790

  Caturla, Francisco ^a   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; PELLITORINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030200291     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00936-7     Document Type: Article

References (37)

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17. (c) See note 27 in previous reference 5b.
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19. 7. Purchased from Aldrich.
20. 10
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24. 10
25. 12. The dilithiation of acid 5a and reaction with electrophiles gave lower yields.
26. 13. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927-1930.
27. 14. The structure of this dianion could be represented by as exo and/or s-trans conformations as has been proposed for the dienolate of 2-butenoic acid: (a) Aurell, M. J.; Gil, S.; Mestres, R.; Parra, M.; Tortajada, A. Tetrahedron 1994, 50, 5109-5118.
28. (b) Domingo, L. R.; Gil, S.; Mestres, R.; Picher, M. T. Tetrahedron 1995, 51, 7207-7214.
29. erythro = 1-2.5 Hz.
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33. 20 (e. g. paralyzing effect on houseflies). For recent synthesis see: (a) Kaga, H.; Ahmed, Z.; Gotoh, K.; Orito, K. Synlett 1994, 607-608.
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37. 22. For other stereoselective synthesis of (2E,4E)-dienamides see: Bernabeu, M. C.; Chinchilla, R.; Nájera, C. Tetrahedron Lett. 1995, 36, 3901-3904 and references cited therein.