Unusual Reactivity of Nitronates with an Aryl Alkyl Carbonate: Synthesis of alpha-Amino Esters

Abstract

The monoanions of nitroalkanes are ambident nucleophiles that react with carbonate electrophiles through the oxygen atom. Products arising from reactivity at the carbon atom will yield alpha-nitro esters, which are precursors for alpha-amino esters. We demonstrate this in the reactions of nitroalkanes with benzyl phenyl carbonate and DABCO where alpha-nitro esters are obtained instead of nitrile oxides. The products are readily reduced to alpha-amino esters. This pathway could be a safe alternative to the Strecker reaction.