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 language | English |
|---|---|
| Journal | Chemical Science |
| Volume | 8 |
| Issue number | 12 |
| Pages (from-to) | 7978-7982 |
| Number of pages | 5 |
| ISSN | 2041-6520 |
| DOIs | |
| Publication status | Published - 2017 |
Cite this
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Thiosemicarbazone organocatalysis : Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation. / Larsen, Dennis; Langhorn, Line M.; Akselsen, Olivia M.; Nielsen, Bjarne E.; Pittelkow, Michael.
In: Chemical Science, Vol. 8, No. 12, 2017, p. 7978-7982.Research output: Contribution to journal › Journal article › Research › peer-review
TY - JOUR
T1 - Thiosemicarbazone organocatalysis
T2 - Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation
AU - Larsen, Dennis
AU - Langhorn, Line M.
AU - Akselsen, Olivia M.
AU - Nielsen, Bjarne E.
AU - Pittelkow, Michael
PY - 2017
Y1 - 2017
N2 - 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.
AB - 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.
U2 - 10.1039/c7sc03366d
DO - 10.1039/c7sc03366d
M3 - Journal article
C2 - 29568444
AN - SCOPUS:85034828020
VL - 8
SP - 7978
EP - 7982
JO - Chemical Science
JF - Chemical Science
SN - 2041-6520
IS - 12
ER -