Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: one-pot syntheses of highly functional alkenes

Org Biomol Chem. 2011 Jan 21;9(2):363-6. doi: 10.1039/c0ob00644k. Epub 2010 Nov 4.

Abstract

An EtPPh(2)- or PPh(3)-catalyzed tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide is developed. Its further application in one-pot syntheses of highly functional alkenes starting from aldehydes, alkyl vinyl ketones, and amides is realized. A wide variety of highly functional α,β-unsaturated ketones can be furnished in 68-99% yields with high stereoselectivity (E/Z up to 98 : 2) within overall 3-29.5 h.