Lewis acid-catalyzed oxidative allylation: A new approach for the synthesis of homoallylic alcohols and amines directly from alcohols

Abstract

A new approach for the synthesis of homoallylic alcohols and amines directly from alcohols via one-pot sequential oxidation-Barbier reaction and oxidation-condensation-Barbier reactions, respectively, is reported. The protocol involves the one-pot ferric chloride-catalyzed oxidation of alcohols to the corresponding aldehydes with chloramine-T followed by indium-mediated Barbier allylation with allyl bromide to afford homoallylic alcohols in 70-90% overall yields. The ferric chloride-catalyzed condensation of aldehydes and oxidation by-product p-toluenesulfonamide followed by indium-mediated Barbier-type allylation of the resulting aldimines with allyl bromide affords homoallylic amines in 60-80% overall yields in the same reaction vessel. The present work demonstrates a new one-pot approach toward homoallylic alcohol and amine synthesis directly from alcohols. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.