High pressure promoted aza-Michael addition of primary and secondary amines to α-substituted acrylates

Abstract

The α-dialkoxymethyl α,β-unsaturated ester 1 can be easily converted, under high pressure and at ambient temperature, into the corresponding aza-Michael adducts 2 and/or push–pull α-aminomethyl-β-methoxy-α,β-unsaturated esters 3 by treatment with primary or secondary amines. The ratio between these two types of products is shown to depend on the nature of the nitrogen nucleophile.