Thioperoxide-Mediated Activation of Thioglycoside
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Posted on 2014-06-06 - 00:00
Thioperoxide
(1) in combination with trimethylsilyl
trifluoromethanesulfonate (TMSOTf) provides a powerful
thiophilic promoter system, capable of activating different thioglycosides.
Both armed and disarmed thioglycosides were activated effectively
in the presence of different glycosyl acceptors, giving glycosidation
products in high to excellent yields. A plausible activation pathway
was also proposed and supported by isolating side-products trifluoromethylphenyl
disulfide (CF3SSPh) and alkene (42).