Allylation of β-ketoaldehydes and functionalized imines by diallyltin dibromide: Formation of skipped and conjugated dienes

Abstract

Diallyltin dibromide reacts with β-ketoaldehydes possessing no aromatic side groups and with (hydroxy) aryl imines to afford the expected homoallyl alcohols or amines respectively. With β-ketoaldehydes having aromatic side groups, skipped or conjugated dienes are obtained depending on whether or not an aqueous work up procedure is used.