Ferrocene-based P -chiral amidophosphinate: stereoselective synthesis and X-ray structural study.

Racemic and enantiopure ferrocene-based P -chiral amidophosphinates have been simply and stereoselectively synthesized by ortho -lithiation of rac - or ( R )-Ugi's amine and further reaction with amidochlorophenylphosphinate Cl-P(O)(Ph)NEt 2 . This is the first example of an asymmetric reaction of ortho -lithiated Ugi's amine with tetracoordinated phosphorus(V) chlorides. The structures of rac - and ( R )-Ugi's amine ferrocenyl(phenyl)phosphinic acid N , N -diethylamide have been extensively studied experimentally (NMR, X-ray analysis, electrochemistry). The CV first peak refers to the oxidation of the amine fragment, which is clearly seen when ( R )-Ugi's amine ferrocenyl(phenyl)phosphinic acid N , N -diethylamide reacts with anhydrous acid. The addition of two equivalents of CF 3 COOH leads to the protonation of nitrogen atoms, and a classical reversible wave of oxidation of Fe(II) to Fe(III) is observed.