Efficient synthesis of (E)-2-nitromethylcinnamates via phosphine-catalyzed tandem α-addition and 1,3-rearrangement

Abstract

An efficient synthesis of (E)-2-nitromethylcinnamates via a phosphine-catalyzed reconstitutive addition of aryl-substituted nitromethanes to alkynes is described. In this tandem event, initial α-umpolung addition of activated alkynes with nitromethanes generates the terminal alkene intermediates which further undergo 1,3-rearrangement of the nitro subunit to produce the title compounds. The substituted cinnamate derivatives can be easily transformed into useful products, and this novel cascade protocol may open new opportunities to access interesting molecular structures.