An enantioselective synthesis of (R)-2-amino-1-hydroxyethylphosphonic acid by hydrolytic kinetic resolution of (±)-diethyl oxiranephosphonate

Article abstract of DOI:10.1016/S0040-4039(99)01259-9

(±)-Diethyl oxiranephosphonate undergoes efficient hydrolytic kinetic resolution by (R,R)-N,N'-bis(3,5-di-tertbutylsalicylidene)-1,2- cyclohexanediaminocobalt(III) acetate; opening of the resultant (R)-epoxide by benzylamine, followed by phosphonate ester hydrolysis and hydrogenolysis, affords the protozoal plasma membrane component (R)-2-amino-1- hydroxyethylphosphonic acid.