Stereospecific cyclization reaction of alkenyl esters and amides of ethenetricarboxylate

Abstract

The stereospecificity of the cyclization reaction of (E)- and (Z)-2-alkenyl esters and amides of ethenetricarboxylate has been examined. The reaction of (E)/(Z)-2-butenyl esters with AlCl3 or FeCl3 gave trans-substituted chlorinated γ-lactone diastereomers stereospecifically. (E)/(Z)-2-butenyl and pentenyl amides undergo an intramolecular ene reaction at room temperature gradually. At 80 °C, the (Z)-alkenyl amides were transformed to cis-substituted ene adducts and the (E)-amides were transformed to cis- and trans-substituted ene adduct mixtures. The reaction of (E)/(Z)-2-alkenyl amides with ZnI2 gave trans-substituted γ-lactam diastereomers stereospecifically along with the ene adducts.