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Issue 12, 2017
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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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Supplementary files

Article information


Submitted
02 Aug 2017
Accepted
27 Sep 2017
First published
06 Oct 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 7978-7982
Article type
Edge Article

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, 8, 7978
DOI: 10.1039/C7SC03366D

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