Nesterov V. Asymmetric reduction of ketophosphonates

Optically active ?- and ?-hydroxyphosphonic acids. Development of effective methods for asymmetric reduction of ketophosphonates and their use in the synthesis of phosphoric analogues of natural compounds. Chemical synthesis, chromatography, NMR- and IR-spectroscopy, element analysis, computer design. An efficient and versatile methods for the asymmetric reduction of ?- and ?-ketophosphonates using accessible chiral reactants derived from sodium borohydride and L-(+)- or D-(-)-tartaric acids as well as sodium borohydride and L-Pro are developed. The reduction of ketophosphonates by these reagents led to the corresponding hydroxyphophonates with high chemical and stereochemical purity. The approach developed allows to obtain both optical antipodes of stereochemically pure hydroxyphosphonates. The methodology was used for the asymmetric synthesis of chiral organophosphorus compounds interesting as synthetic blocks (chirons). Were prepared enantiomerically pure phosphonic analogues of natural hydroxyaminoacids - phosphocarnitine and 3-amino-2-hydroxypropylphosphonic acid. Sphere of use - bioorganic and organic chemistry.