Regenerative
Glycosylation under Nucleophilic Catalysis
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Abstract
This article describes 3,3-difluoroxindole
(HOFox)-mediated glycosylation.
The uniqueness of this approach is that both the in situ synthesis
of 3,3-difluoro-3<i>H</i>-indol-2-yl (OFox) glycosyl donors
and activation thereof can be conducted in a regenerative fashion
as is a typical reaction performed under nucleophilic catalysis. Only
a catalytic amount of the OFox imidate donor and a Lewis acid activator
are present in the reaction medium. The OFox imidate donor is constantly
regenerated upon its consumption until glycosyl acceptor has reacted