TY - JOUR A1 - Tatina, Madhu Babu A1 - Mengxin, Xia A1 - Peilin, Rao A1 - Judeh, Zaher M. A. T1 - Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides JF - Beilstein Journal of Organic Chemistry PY - 2019/// VL - 15 SP - 1275 EP - 1280 SN - 1860-5397 DO - 10.3762/bjoc.15.125 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.15.125 KW - C- KW - O- KW - N- and S-linked glycosides KW - enosides KW - Ferrier-rearrangement KW - organocatalyst KW - pseudo-glycosides N2 - 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. ER -