Abstract
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 )-1,2-epoxyalkylphosphonate in good yield and completely chemoselectively without
the formation of the 1,3-dipolar cycloaddition product 1,3-dioxolane.
Key words
1,2-epoxyalkylphosphonates - rhodium acetate - epoxidation - stereoselectivity
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