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Title: Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides
Authors: Tatina, Madhu Babu
Xia, Mengxin
Rao, Peilin
Judeh, Zaher M. A.
Keywords: Engineering::Chemical engineering
Issue Date: 2019
Source: Tatina, M. B., Xia, M., Rao, P., & Judeh, Z. M. A. (2019). Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides. Beilstein Journal of Organic Chemistry, 15, 1275-1280. doi:10.3762/bjoc.15.125
Journal: Beilstein Journal of Organic Chemistry
Abstract: A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.
ISSN: 1860-5397
DOI: 10.3762/bjoc.15.125
Rights: © 2019 Tatina et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License ( Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( The definitive version of this article is the electronic one which can be found at: doi:10.3762/bjoc.15.125
Fulltext Permission: open
Fulltext Availability: With Fulltext
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