Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles

Wei Wen Tan, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)

Abstract

In the presence of a copper(ii) catalyst, enolizable imines bearing various N-substituents and α-diazo-β-ketoesters undergo denitrogenative and dehydrative condensation to afford highly substituted pyrroles in moderate to good yields with exclusive regioselectivity. The reaction likely involves nucleophilic addition of the imine nitrogen to a copper carbenoid, tautomerization of the resulting azomethine ylide to an α-enaminoketone, and a subsequent enamine-ketone cyclocondensation. With Yb(OTf)3 as a unique cocatalyst, α-diazo-β-diketones also participate in the same condensation reaction. The present reaction is applicable to acyclic, exocyclic, and endocyclic imines with tolerance of a broad range of functional groups and heterocyclic moieties, thus opening a new convenient route for the synthesis of the lamellarin family of natural products.

Original languageEnglish
Pages (from-to)6448-6455
Number of pages8
JournalChemical Science
Volume6
Issue number11
DOIs
Publication statusPublished - 2015 Aug 3
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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