Abstract
Lipoic acid is a coenzyme for the oxidative decarboxylation of α-ketoacids in living systems. In this article we describe some applications of lipoic acid derivatives to organic reactions utilizing its redox function.Lipoamide and its polymer derivatives were demonstrated to work as acyl carriers to form amides by the combination of their reductive acylation and oxidative acyl transfer reactions.Dihydrolipoamide, a reduced form of lipoamide, produced an active complex with ferrous ion which was effective for the selective reduction of N-O linkages in hydroxylamines, isoxazolidines, isoxazoles, and nitrobenzenes under mild conditions.Across a polyglutamide membrane having lipoamide structure, a redox reaction proceeded presumably by a thiol-disulfide exchange reaction between polymeric lipoamide units, which worked as electron carriers.
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