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

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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.

Graphical abstract: Thiosemicarbazone organocatalysis: tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation

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Publication details

The article was received on 02 ágú. 2017, accepted on 27 sep. 2017 and first published on 06 okt. 2017


Article type: Edge Article
DOI: 10.1039/C7SC03366D
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    Thiosemicarbazone organocatalysis: tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation

    D. Larsen, L. M. Langhorn, O. M. Akselsen, B. E. Nielsen and M. Pittelkow, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC03366D

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