Hydroxy Group Directed Catalytic Hydrosilylation of Amides

• DOI: 10.1021/acs.orglett.8b03014
• Publication Date: 2018-11-12T17:51:14Z
• Authors: Jizhi Ni; Tsubasa Oguro; Taka Sawazaki; Youhei Sohma; Motomu Kanai
• Keywords: 01 natural sciences; 0104 chemical sciences

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.