Rhodium Acetate-Mediated Epoxidation from the Reaction of Diazobenzylphosphonates with Aldehydes and a Ketone: A Convenient and Highly Stereoselective Synthetic Method of cis-1,2-Epoxypropylphosphonates

The first stereoselective synthetic route to 1,2-epoxyalkylphosphonates from the reaction of dimethyl diazophosphonate with aldehydes or a ketone using a dirhodium complex as catalyst is reported. The experimental results showed that only a single isomer of the epoxide product was obtained from the catalytic reaction, which gave (1R*,2S*)-(Z)-1,2epoxyalkylphosphonate in good yield and completely chemoselectively without the formation of the 1,3-dipolar cycloaddition product 1,3-dioxolane.