Microwave-assisted synthesis of α-aminophosphonates and related derivatives by the Kabachnik-Fields reaction

Abstract

In this paper, the solvent- and catalyst-free synthesis of α-aminophosphonate derivatives is presented by the microwave-assisted Kabachnik-Fields reaction of amines, paraformaldehyde and P-reagents. Starting from >P(O)H compounds bearing different substituents on the phosphorus atom, P-chiral α-aminophosphonates and α-aminophosphinates were prepared, while using an optically active amine, the synthesis of C-chiral derivatives was elaborated. An optically active bisaminophosphine, obtained after double deoxygenation, was utilized as a chiral bidentate aminophosphine ligand in the synthesis of an optically active cyclic platinum complex. As an extension towards α-aminophosphonates containing a functionalizable group, N-hydroxyethyl-α-aminophosphonates were also prepared.

Graphical Abstract

Keywords:

• Kabachnik-Fields reaction
• chiral α-aminophosphonates
• N-hydroxyethyl-α-aminophosphonates
• microwave

Additional information

Funding

The project was supported by the Hungarian Research Development and Innovation Fund (FK123961 and K119202), in part by the ÚNKP-18-3-III-BME-251 New National Excellence Program of the Ministry of Human Capacities (Á.T.).