Cobalt-Catalyzed Asymmetric Hydrosilylation of ?-Oxygenated Ketones

An asymmetric hydrosilylation of alpha-oxygenated ketones was developed under the catalysis of Co(OAc)2 in combination with a chiral phosphine-amido-oxazoline (PAO) ligand, providing a mild, efficient, and enantioselective access to a variety of synthetically useful 1,2-diol derivatives. This protocol can be carried out at the gram scale with a catalyst loading of 1 mol %, and its synthetic utility was demonstrated by efficient conversion of the optically enriched products into chiral alpha-hydroxy acid, 1,3dioxolan-2-one, ethylene oxide, and 1,2,3-1H-triazole.

Automated summary

An asymmetric hydrosilylation of alpha-oxygenated ketones was developed using Co(OAc)2 as the catalyst in combination with a chiral PAO ligand. This method provides a mild, efficient, and enantioselective access to a variety of synthetically useful 1,2-diol derivatives. The synthetic utility of this protocol was demonstrated by efficient conversion of the optically enriched products into chiral alpha-hydroxy acid, 1,3-dioxolan-2-one, ethylene oxide, and 1,2,3-1H-triazole.