Iodine-mediated direct α-amination of dimethyl methylmalonate using non-protected amines

Abstract

In this study, direct CN bond formation was achieved via the reaction of a dimethyl methylmalonate with various amines in the presence of molecular iodine to produce α-aminocarbonyl compounds. This versatile methodology of the α-amination of a carbonyl-containing compound involves the in situ iodination of the dimethyl methylmalonate, thus promoting the formation of its enolate isomer, which then facilitates its nucleophilic substitution reaction with an amine. This strategy is highly practical and can be used in industry due to its requirement of only readily available reagents without any pre-preparation of the amines and other substrates.