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Issue 5, 2015
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Enantioselective α-amination of 1,3-dicarbonyl compounds in batch and flow with immobilized thiourea organocatalysts

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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

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Article information


Submitted
04 Mar 2015
Accepted
02 Apr 2015
First published
02 Apr 2015

Green Chem., 2015,17, 3122-3129
Article type
Paper
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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