Please use this identifier to cite or link to this item:
|Title:||Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds : modular and regiocontrolled synthesis of multisubstituted pyrroles||Authors:||Tan, Wei Wen
|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.||URI:||https://hdl.handle.net/10356/89964
|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|
Files in This Item:
|Copper catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds modular and regiocontrolled synthesis of multisubstituted pyrroles.pdf||999.03 kB||Adobe PDF|
Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.