Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst
АуториStevanović, Dragana D.
Damljanović, Ivan S.
Bogdanović, Goran A.
Radulovic, Niko S.
Vukicevic, Rastko D.
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In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-D-glucal and 6-deoxy-3,4-di-O-acetyl-L-glucal (3,4-di- O-acetyl-L-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol(-1)) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio alpha/beta-4.129 in the case of peracetylated D-glucal and 8.740 in the case of L-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives (C-glycosides) using allyltrimethylsilane as the nucleophile (only alpha-anomers were obtained). All new compounds were fully characterized by spectral data, whereas s...ingle-crystal X-ray analysis was performed for two thioglycosides. (C) 2015 Elsevier Ltd. All rights reserved.