Thiosemicarbazone organocatalysis: Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation

Dennis Larsen, Line M. Langhorn, Olivia M. Akselsen, Bjarne E. Nielsen, Michael Pittelkow*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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Abstract

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.

Original languageEnglish
JournalChemical Science
Volume8
Issue number12
Pages (from-to)7978-7982
Number of pages5
ISSN2041-6520
DOIs
Publication statusPublished - 2017

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