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Glycosylation Catalyzed by a Chiral Brønsted Acid

Daniel J. Cox, Martin D. Smith and Antony J. Fairbanks*

*Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand, Email: antony.fairbankscanterbury.ac.nz

D. J. Cox, M. D. Smith, A. J. Fairbanks, Org. Lett., 2010, 12, 1452-1455.

DOI: 10.1021/ol1001895 (free Supporting Information)


Abstract

The use of a chiral Brønsted acid catalyst for the activation of trichloroacetimidate glycosyl donors influences the stereochemical outcome of glycosylation processes in toluene, hinting that perhaps diastereocontrol may become achievable through the judicious use of chiral organic catalysts.

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Key Words

Acetals, Organocatalysis


ID: J54-Y2010-0880