Metal free chemoselective reduction of α-keto amides using TBAF as catalyst†
N. Chary Mamillapalli,Govindasamy Sekar
RSC Advances Pub Date : 11/06/2014 00:00:00 , DOI:10.1039/C4RA13090A
Abstract

The metal and ligand free chemoselective reduction of the keto group and complete reduction of the both keto and amide groups of α-keto amide with hydrosilanes using tetrabutylammoniumflouride (TBAF) as catalyst have been accomplished. This methodology affords an efficient and economic route for the synthesis of biologically important α-hydroxy amides and β-amino alcohols. The other important advantage of this TBAF catalyst is chemoselective reduction of ketones to corresponding alcohols in the presence of several other sensitive functional groups.

Graphical abstract: Metal free chemoselective reduction of α-keto amides using TBAF as catalyst