Convergent Synthesis of Dihydropyrans from Catalytic
Three-Component Reactions of Vinylcyclopropanes, Diazoesters, and
Diphenyl Sulfoxide
Posted on 2020-06-30 - 19:14
A novel
Rh(I)/La(III) cocatalytic three-component reaction of vinylcyclopropanes,
diazoesters, and diphenyl sulfoxide has been developed. The reaction
gives polysubstituted dihydropyrans as the reaction products. Mechanistic
studies indicate that isomerization of vinylcyclopropanes gives conjugated
dienes, which then undergo [4 + 2]-cycloaddition with vicinal tricarbonyl
compounds generated by oxygen atom transfer from diphenyl sulfoxide
to diazoesters.
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Zhang, Ya-Lin; Guo, Rui-Ting; Luo, Heng; Liang, Xin-Shen; Wang, Xiao-Chen (2020). Convergent Synthesis of Dihydropyrans from Catalytic
Three-Component Reactions of Vinylcyclopropanes, Diazoesters, and
Diphenyl Sulfoxide. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.0c01992