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Назив: Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst
Аутори: Stevanović, Dragana
Pejović, Anka
Damljanović, Ivan
Minić, Aleksandra
Bogdanovic, Goran A.
Vukićević, Miomir
Radulovic, Niko
Vukicevic R.
Датум издавања: 2015
Сажетак: © 2015 Elsevier Ltd. All rights reserved. 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<sup>-1</sup>) 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 α/β=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 'α-anomers' were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides.
URI: https://scidar.kg.ac.rs/handle/123456789/12034
Тип: article
DOI: 10.1016/j.carres.2015.02.001
ISSN: 0008-6215
SCOPUS: 2-s2.0-84923858552
Налази се у колекцијама:Faculty of Science, Kragujevac

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