Abstract
Fluoroboronic acid adsorbed on silica gel (HBF4 ˙SiO2 ) catalyzes
the Ferrier rearrangement of per-O-acetylated glycals with alcohols
and sulfonamides to give 2,3-unsaturated O -
and N -glycosides in good to excellent
yield and with high α-stereoselectivity.
Key words
glycosylations - green chemistry - Ferrier
rearrangement -
N -glycosylsulfonamides -
O -glycosides
References and Notes
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Experimental Procedure
in vacuo. The residue
was chromatographed on SiO2 (eluent hexane-EtOAc)
to afford the glycosides.Preparation
of HBF
4
˙SiO
2
2 (13.4 g, 230-400 mesh) in
Et2 O (37 mL) was treated with 40% aq HBF4 (1.5 g)
for 3 h. The mixture was concentrated and the residue dried under
vacuum at 100 ˚C for 24 h to afford HBF4 ˙SiO2 (0.5
mmol g-¹ ).
[³0
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MHz) spectra of the glycosides confirmed the α-configuration
of the products formed in the reactions by comparison with the literature
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