Rhenium(V)-catalyzed synthesis of 2-deoxy-alpha-glycosides.
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.
Sherry
Benjamin D
BD
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, USA.
Loy
Rebecca N
RN
Toste
F Dean
FD
D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012211:Rhenium / Q000737:chemistry*
D006027:Glycosides; D012211:Rhenium