Kabachnik

The Kabachnik–Fields reaction is a three-component chemical reaction forming α-amino phosphonates from an amine, a carbonyl compound (aldehyde or ketone), and a dialkyl phosphite. This reaction is named after M. I. Kabachnik and E. K. Fields, who independently reported the reaction in the early 1950s.

The α-amino phosphonates produced in the Kabachnik–Fields reaction are valuable building blocks in organic synthesis, finding applications as peptidomimetics, enzyme inhibitors, and pharmacological agents. They contain both amino and phosphonate functionalities, offering diverse possibilities for further chemical modifications.

The reaction mechanism generally involves the initial formation of an imine (from the amine and carbonyl compound) or a carbonyl compound activated by a phosphite via proton transfer, followed by nucleophilic attack of the dialkyl phosphite on the imine or carbonyl, resulting in the α-amino phosphonate product. The reaction can be catalyzed by acids, bases, or Lewis acids. Variations of the reaction have also been developed, including solvent-free conditions and the use of different catalysts to improve reaction rates and yields.