Canadian Journal of Chemistry p. 523 - 530 (1997)
Update date:2022-08-29
Topics:
Belaissaoui, Abdelhak
Jacquot, Sandrine
Morpain, Claude
Schmitt, Gerard
Vebrel, Joel
Laude, Bernard
The reaction of ethyl diazoacetate with the N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine yields, by a nucleophilic addition, a new diazo compound that gives 1,3-dipolar cycloaddition reactions with acetylenic esters and maleimides. With acetylenic esters, the cycloadduct leads to substituted pyrazoles by [1,5] sigmatropic rearrangements. With maleimides, we observe a diastereospecific cycloaddition reaction. The intermediary cycloadduct evolves by nitrogen elimination to give a maleimidocyclopropane. The diastereospecificity was explained by an endo-anti approach of the reactants.
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