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Issue 31, 2017
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A copper-templated, bifunctional organocatalyst: a strongly cooperative dynamic system for the aldol reaction

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Abstract

The study of novel metal-templated dynamic organocatalytic systems has led to the identification of CuSO4 as the most efficient template to assemble monofunctional prolinamide- and thiourea-modified pyridine ligands. The structural and electronic requirements to assemble an efficient catalyst have been disclosed: both pyridine ligands must bear a 1,3-substitution pattern, and the thiourea ligand serves as a reducing agent to copper(I) as well. Eventually, the cooperative effects achieved with such a simple system deliver high reaction rates and stereoselectivities at room temperature in the asymmetric aldol reaction, requiring only 1 mol% of copper salt.

Graphical abstract: A copper-templated, bifunctional organocatalyst: a strongly cooperative dynamic system for the aldol reaction

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Publication details

The article was received on 06 Jun 2017, accepted on 17 Jul 2017 and first published on 17 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01370A
Citation: Org. Biomol. Chem., 2017,15, 6584-6591
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    A copper-templated, bifunctional organocatalyst: a strongly cooperative dynamic system for the aldol reaction

    A. Serra-Pont, I. Alfonso, J. Solà and C. Jimeno, Org. Biomol. Chem., 2017, 15, 6584
    DOI: 10.1039/C7OB01370A

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