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

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Abstract

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 via 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.

Graphical abstract: Stereoselective organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings

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Publication details

The article was received on 25 Jun 2018, accepted on 15 Oct 2018 and first published on 22 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC02788A
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Stereoselective organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings

    G. A. Bradshaw, A. C. Colgan, N. P. Allen, I. Pongener, M. B. Boland, Y. Ortin and E. M. McGarrigle, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC02788A

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