α-Ketiminophosphonates: Synthesis and Applications

Abstract

The synthesis of α-iminophosphonates derived from ketones has been achieved by aza-Wittig reaction of P-trimethylphosphazenes with acylphosphonates. These unstable compounds can be used for the synthesis of chiral α-aminophosphonate derivatives through addition of nucleophiles to the C-N iminic double bond. Moreover, if α,β-unsaturated imines are used, regioselective Michael addition to the conjugated bond yields α-dehydroamino-phosphonic acid derivatives functionalized at the γ-position.

Keywords:

• α-Aminophosphonates
• α-dehydroaminophosphonates
• α-iminophosphonates
• α,β-unsaturated imines

Acknowledgments

The present work has been supported by the Dirección General de Investigación del Ministerio de Ciencia e Innovación (MICINN, Madrid DGI, CTQ2009-12156) and by the Departamento de Educación, Universidades e Investigación del Gobierno Vasco and Universidad del País Vasco (GV, IT 422-10; UPV, GIU-09/57). J. V. thanks the Ministerio de Ciencia e Innovación for a “Ramón y Cajal” contract.