The conversion of olefins to β-keto esters: Ozonolysis of olefins followed by in situ reduction with tin(II) chloride in the presence of ethyl diazoacetate

Article abstract of DOI:10.1016/S0040-4039(00)97786-4

Trisubstituted olefins are converted to β-keto esters by treatment with ozone followed by the addition of tin(H) chloride and ethyl diazoacetate. Monosubstituted olefins are first treated with ozone in the presence of methanol to generate methoxy hydroperoxides. The hydroperoxides are subsequently reduced with tin(II) chloride in the presence of ethyl diazoacetate to produce β-keto esters.