Issue 31, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
06 Jun 2017
Accepted
17 Jul 2017
First published
17 Jul 2017

Org. Biomol. Chem., 2017,15, 6584-6591

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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