Chiral ketone- or chiral amine-catalyzed asymmetric epoxidation of cis-1-propenylphosphonic acid using hydrogen peroxide as oxidant

Abstract

By using a d-fructose-derived chiral ketone or a d-mannitol-derived chiral amine as catalyst, the organocatalytic asymmetric epoxidation of cis-1-propenylphosphoric acid with 30% aqueous hydrogen peroxide in H 2O–CH 3CN mixture (∼80:20) afforded (1 R, 2 S)-(−)-(1,2)-epoxypropyl phosphoric acid (fosfomycin). Asymmetric epoxidation was carried out at 0 °C for 72 h to achieve 100% conversion with a maximum enantiomeric excess (e.e.) of 74%.