Stereoselective synthesis of 2,4-dioxo-5-phenyl-1- phenylethylamino-4-phenoxy-1,3,4-dazaphospholidine

Recently we showed that diphenyl (α-methylamino) benzylphosphonate easily added to phenyl isocyanate or phenyl isothiocyanate in the presence of a catalytic amount of triethylamine affording N,N'-substituted (thio)ureas; cyclization of the latter led to the formation of 1,3,4-diazaphospholidines [1]. Now we studied reaction of bis(chloromethyl)isocyanatophosphinate (I) with optically active diphenyl(α-methylamino)benzylphosphonate (II). Noteworthy that the formation of the latter compound was registered recently in the reaction of catalytic addition of diphenyl hydrogen phosphite to the optically active (S)-(–)-benzal(1-phenyl)ethylamine (catalyst BF3) by Р NMR spectroscopy as a mixture of stereoisomers which was not separated [2]. We obtained optically active aminophosphonate II in the same reaction using sodium phenolate as a catalyst: DOI: 10.1134/S1070363208120190