Synthesis of functionalized organophosphorus analogs of α- and β-alanine

Abstract

Convenient syntheses of organophosphorus analogs of α- and β-alanine containing functionalized phosphonous and phosphinic acid moieties based on readily available trimethylsilyl esters of trivalent phosphorus acids have been developed. Nucleophilic addition of bis(trimethylsiloxy)phosphine to trimethylsilyl acrylates or α-(acetylamino)-acrylates proceeds regioselectively to give [2-(trimethylsiloxycarbonyl)ethyl]phosphonites, the subsequent functionalization of which affords various derivatives of the target acids. The resulting compounds are of interest as promising biologically active substances and water-soluble ligands.