Kabachnik–Fields reaction

In organophosphorus chemistry, the Kabachnik–Fields reaction is a three-component organic reaction forming α-aminomethylphosphonates from an amine, a carbonyl compound, and a dialkyl phosphonate, (RO)2P(O)H (that are also called dialkylphosphites).

[1] Aminophosphonates are synthetic targets of some importance as phosphorus analogues of α-amino acids (a bioisostere).

This multicomponent reaction was independently discovered by Martin Kabachnik [ru][2][3] and Ellis K. Fields[4] in 1952.

The reaction can be accelerated with a combination of dehydrating reagent and Lewis acid.

Enantioselective variants of the Kabachnik-Fields reaction have been developed, for example employing α-methylbenzylamine provides a chiral, non-racemic α-aminophosphonate.