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

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 H2O–CH3CN mixture (∼80:20) afforded (1R, 2S)-(−)-(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%.

Graphical abstractBy using a d-fructose-derived chiral ketone or a d-mannitol-derived chiral amine as catalyst and 30% aqueous hydrogen peroxide as oxidant, the organocatalytic asymmetric epoxidation of cis-1-propenylphosphoric acid afforded (1R, 2S)-(−)-(1,2)-epoxypropyl phosphoric acid. At 0 °C for 72 h, the enantiomeric excess (e.e.) reached 74% at 100% conversion.Figure optionsDownload full-size imageDownload as PowerPoint slide