Stereoselective organocatalyzed glycosylations - thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings

Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%. It is proposed that in these glycosylations thiouracil, monothiophthalimide, and the previously reported catalyst, Schreiner's thiourea, do not operate a double H-bonding mechanism but rather by B...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-01, Vol.10 (2), p.508-514
Main Authors: Bradshaw, G A, Colgan, A C, Allen, N P, Pongener, I, Boland, M B, Ortin, Y, McGarrigle, E M
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Chemical synthesis
NMR
Nuclear magnetic resonance
Stereoselectivity
Sugar
Thioureas
Trehalose
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Summary:Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%. It is proposed that in these glycosylations thiouracil, monothiophthalimide, and the previously reported catalyst, Schreiner's thiourea, do not operate a double H-bonding mechanism but rather by Brønsted acid/base catalysis. In addition to the synthesis of 2-deoxyglycosides and glycoconjugates, we report the first organocatalytic synthesis of 1,1'-linked trehalose-type sugars.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc02788a