Beilstein J. Org. Chem.2019,15, 1275–1280, doi:10.3762/bjoc.15.125
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.
Keywords: C-; O-; N- and S-linked glycosides; enosides; Ferrier-rearrangement; organocatalyst
; pseudo-glycosides; Introduction
2,3-Unsaturated glycosides, also known as pseudo-glycosides or enosides, are an important class of natural products with many biological activities and capacity to serve as substrates for further reactions [1][2][3]. They are involved in biochemical processes such as
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Graphical Abstract
Figure 1:
Perfluorophenylboronic acid-catalyzed reaction between 3,4,6-tri-O-acetyl-D-glucal 1a and O-, C-, S...