Intercepting the Nazarov Oxyallyl Intermediate with -Formylvinyl Anion Equivalents to Access Formal Morita-Baylis-Hillman Alkylation Products

Abstract

A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing -formylvinyl functionality which is formally equivalent to products of a Morita-Baylis-Hillman alkylation process.