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Multicomponent Synthesis of Pyrroles from Cyclopropanes: A One-Pot Palladium(0)-Catalyzed Dehydrocarbonylation/Dehydration


  • We thank the Natural Sciences and Engineering Research Council (NSERC) for funding. We are grateful to Doug Hairsine for performing MS analyses. The term dehydrocarbonylation refers to a dehydrogenative decarbonylation.


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Ring the changes: The cycloaddition of nitrones with 1-carboallyloxy-1-carbomethoxycyclopropanes yields tetrahydro-1,2-oxazines, which in turn undergo a Tsuji dehydrocarbonylation to give dihydro-1,2-oxazines (see scheme; dba=dibenzylideneacetone). Addition of base to this reaction mixture results in clean conversion to pyrroles. The result is a flexible three-component strategy for the synthesis of tetrasubstituted pyrroles.

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