Hydroxy Group Directed Catalytic Hydrosilylation of Amides

Chemo- and site-selective hydrosilylation of α- or β-hydroxy amides using organocatalyst B(C₆F₅)₃ and commercially available hydrosilanes is described. This transformation is operative under mild conditions and tolerates a wide range of functional groups. The reaction was applied for selective reduction of a specific amide group of the therapeutically important cyclic peptide cyclosporin A, demonstrating the potential usefulness of this catalytic method in late-stage structural transformations of drug lead molecules.