(2E)-4-Methoxy-2,4-pentadienamides as New Dienes in the Diels-Alder Reaction
- Bernabeu, M.C. 1
- Chinchilla, R. 1
- Nájera, C. 1
- Rodríguez, M.A. 2
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1
Universitat d'Alacant
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2
Universidad de La Rioja
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ISSN: 0040-4039
Year of publication: 1996
Volume: 37
Issue: 20
Pages: 3595-3598
Type: Article
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Abstract
(2E)-4-Methoxy-2,4-pentadienamides have been stereoselectively prepared by treatment of (2E,4E)-5-tosyl-2,4-pentadienamides with 1M methanolic potassium hydroxide in good yields. They behave as new electron-rich dienes in Diels-Alder reactions to give stereoselectively highly functionalized adducts 3 mainly with endo-selectivity and, after hydrolysis, only their corresponding cyclohexanone derivatives 4. Semi-empirical calculations corroborate their reactivity.