In this paper, chiral molybdenum(VI) or tungsten(VI) 2'-pyridinyl alcoholate complex catalyzed asymmetric epoxidation of cis-1-propenylphosphonic acid in H₂O was reported. This is an asymmetric epoxidation reaction taking place on the solid-liquid interface. The highest ee value of 71% was achieved by using chiral molybdenum(VI) 2'-pyridingyl alcoholate complex at 0 ℃. After addition of phase transfer catalyst Bu₄NBr, the yield and ee value were remarkably increased. For example, using chiral tungsten(VI) 2'-pyridinyl alcoholate complex at 50 ℃, the ee value was increased from 54% to 78%.

Key words: cis-1-propenylphosphonic acid, heterogeneous catalytic reaction, fosfomycin, chiral 2'-pyridinyl alcoholate complex, catalytic asymmetric epoxidation