1.
Chem Sci
; 8(12): 7978-7982, 2017 Dec 01.
Article
in English
| MEDLINE
| ID: mdl-29568444
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.