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Title: Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds : modular and regiocontrolled synthesis of multisubstituted pyrroles
Authors: Tan, Wei Wen
Yoshikai, Naohiko
Keywords: Condensation
Copper Catalyzed
Issue Date: 2015
Source: Tan, W. W., & Yoshikai, N. (2015). Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles. Chemical Science, 6(11), 6448-6455. doi:10.1039/c5sc02322j
Series/Report no.: Chemical Science
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.
ISSN: 2041-6520
DOI: 10.1039/C5SC02322J
Rights: © 2015 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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