Chemo-selective Rh-catalysed hydrogenation of azides into amines

Abstract

Rh/Al₂O₃ can be used as an effective chemo-selective reductive catalyst that combines the mild conditions of catalytic hydrogenation with high selectivity for azide moieties in the presence of other hydrogenolysis labile groups such as benzyl and benzyloxycarbonyl functionalities. The practicality of this strategy is exemplified with a range of azide-containing carbohydrate and amino acid derivatives.

Keywords: Aminoglycosides; Azide reduction; Chemo-selective reduction; Protecting groups manipulation; Rhodium catalysis.