Acid-Catalyzed Nazarov Reaction Controlled by β-Alkoxy Groups

Abstract

Acid-catalyzed Nazarov reaction of β-alkoxy divinyl ­ketones providing 5-oxycyclopent-2-enones has been developed. The effects of the β-alkoxy group on the catalyst efficiency and the regioselectivity are based on the stabilization of the intermediates and the spontaneous elimination of the group followed by trapping. The substrates are easily accessible using the torquoselective olefination of esters with ynolates.