Issue 5, 2015

Enantioselective α-amination of 1,3-dicarbonyl compounds in batch and flow with immobilized thiourea organocatalysts

Abstract

A polymer-supported bifunctional thiourea organocatalyst (PS-TU) has been prepared and successfully used in the enantioselective α-amination of 1,3-dicarbonyl compounds with azodicarboxylates. In contrast to homogeneous thioureas, PS-TU is not irreversibly deactivated by the azodicarboxylate reagents, and simple washing with triethylamine between runs has allowed the reuse (9 cycles) of the PS-TU catalyst. The α-amination mediated by PS-TU has also been adapted to perform the enantioselective amination (93% ee) of ethyl 2-oxocyclopentanecarboxylate in continuous flow (7.5 h operation, 21 min residence time, TON = 37).

Graphical abstract: Enantioselective α-amination of 1,3-dicarbonyl compounds in batch and flow with immobilized thiourea organocatalysts

Supplementary files

Article information

Article type
Paper
Submitted
04 Mar 2015
Accepted
02 Apr 2015
First published
02 Apr 2015

Green Chem., 2015,17, 3122-3129

Author version available

Enantioselective α-amination of 1,3-dicarbonyl compounds in batch and flow with immobilized thiourea organocatalysts

P. Kasaplar, E. Ozkal, C. Rodríguez-Escrich and M. A. Pericàs, Green Chem., 2015, 17, 3122 DOI: 10.1039/C5GC00496A

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