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 α-nitro esters, which are precursors for α-amino esters. We demonstrate this in the reactions of nitroalkanes with benzyl phenyl carbonate and DABCO where α-nitro esters are obtained instead of nitrile oxides. The products are readily reduced to α-amino esters. This pathway could be a safe alternative to the Strecker reaction.

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A pre‐synthesized stable complex of a novel bis‐camphorsulfonyl urea derivative with two equivalents of NaBPh4 is successfully employed as catalyst for the asymmetric Michael addition of pyrrole or indole to give nitroolefins.

Unusual Reactivity of Nitronates with an Aryl Alkyl Carbonate: Synthesis of -Amino Esters. -The presented method offers a safe and scalable alternative to the well-known Strecker reaction. -(REDDY, G. R.; MUKHERJEE, D.; CHITTOORY, A. K.; RAJARAM*, S.; Org. Lett. 16 (2014) 22, 5874-5877, http://dx.