Primary carbohydrate amines at primary and secondary carbons are alkylated by alcohols in the presence of [Cp*IrCl(2)](2). When primary carbohydrate alcohols are used as the coupling partners and in the presence of Cs(2)CO(3), amine-linked pseudodisaccharides are obtained. Secondary carbohydrate alcohols are unaffected under these conditions, which allows regioselective reactions.
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Cumpstey et al. (2011) studied this question.
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