Journal
CHEMICAL SCIENCE
Volume 8, Issue 12, Pages 7978-7982Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc03366d
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Funding
- Lundbeck Foundation (Young Group Leader Fellowship)
- Danish Council for Independent Research [DFF 4181-00206]
- Department of Chemistry, University of Copenhagen
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The first use of thiosemicarbazone-based organocatalysis was demonstrated on both tetrahydropyranylation and 2-deoxygalactosylation reactions. The organocatalysts were optimised using kinetics-based selection. The best catalyst outperformed previously reported thiourea catalysts for tetrahydropyranylation by 50-fold. Hammett investigations of both the organocatalyst and the substrate indicate an oxyanion hole-like reaction mechanism.
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