(2 E)-4-methoxy-2,4-pentadienamides as new dienes in the Diels-Alder reaction

Abstract

(2 E)-4-Methoxy-2,4-pentadienamides have been stereoselectively prepared by treatment of (2 E,4 E)-5-tosyl-2,4-pentadienamides with IM 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.