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

Author:

Bradshaw G. A.12345,Colgan A. C.12345ORCID,Allen N. P.12345,Pongener I.12345ORCID,Boland M. B.12345,Ortin Y.12345,McGarrigle E. M.12345ORCID

Affiliation:

1. Centre for Synthesis & Chemical Biology

2. UCD School of Chemistry

3. University College Dublin

4. Dublin 4

5. Ireland

Abstract

Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%.

Funder

Irish Research Council

Science Foundation Ireland

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Reference94 articles.

1. G. Jakab and P. R.Schreiner in Comprehensive Enantioselective Organocatalysis , ed. P. Dalko , Wiley-VCH , Weinheim , 2013 , ch. 12, vol. 2

2. K. Hof , K. M.Lippert and P. R.Schreiner in Asymmetric Organocatalysis , ed. K. Maruoka ), Thieme , Stuttgart , 2012 , ch. 2.2.4, vol. 2

3. Small-Molecule H-Bond Donors in Asymmetric Catalysis

4. Theoretical Studies on the Bifunctionality of Chiral Thiourea-Based Organocatalysts:  Competing Routes to C−C Bond Formation

5. Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts

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