Journal
GREEN CHEMISTRY
Volume 17, Issue 5, Pages 3122-3129Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5gc00496a
Keywords
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Funding
- MINECO [CTQ2012-38594-C02-01]
- MINECO (Severo Ochoa Excellence Accreditation) [SEV-2013-0319]
- MINECO (FPI fellowship)
- DEC Generalitat de Catalunya [2014SGR827]
- DEC Generalitat de Catalunya (BP-B fellowship)
- ICIQ Foundation
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A polymer-supported bifunctional thiourea organocatalyst (PS-TU) has been prepared and successfully used in the enantioselective alpha-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 a-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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