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Published on: July 23, 2016
Rhenium(V)-catalyzed synthesis of 2-deoxy-alpha-glycosides
Benjamin D Sherry1, Rebecca N Loy, F Dean Toste
1Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, USA.
Abstract:
A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium-oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-alpha-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.
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