Enantioselective α-amination of 1,3-dicarbonyl compounds in batch and flow with immobilized thiourea organocatalysts?
Green Chemistry Pub Date: 2015-04-02 DOI: 10.1039/C5GC00496A
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).
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Journal Name：Green Chemistry
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CAS no.: 89640-58-4
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