Indium chloride catalyzed alkylative rearrangement of propargylic acetates using alkyl chlorides, alcohols, and acetates: facile synthesis of α-alkyl-α,β-unsaturated carbonyl compounds

Org Lett. 2014 Feb 21;16(4):1176-9. doi: 10.1021/ol500046e. Epub 2014 Feb 4.

Abstract

Indium chloride catalyzed alkylative rearrangement of propargylic acetates into α-alkyl-α,β-unsaturated carbonyl compounds has been achieved. Propargylic acetates functioned as α-acylvinyl anion equivalents to react with carbocations generated from alkyl chlorides. Other alkyl electrophiles such as alcohols and acetates were also applicable.