Methylhydrazine-induced enantioselective α-hydroxylation of β-keto esters with molecular oxygen catalyzed by hydroquinine

Methylhydrazine-induced α-hydroxylation of β-dicarbonyl compounds was achieved using O2 as the oxygen source. This reaction provides an efficient approach to enantioenriched ɑ-hydroxy β-dicarbonyl compounds, which are valuable substances and widely used in the chemical and pharmaceutical industry. A wide variety of β-keto esters could undergo this oxidation to give the corresponding products in excellent yields (up to 95%) and with good enantioselectivities (up to 85% ee). The mild reaction conditions and the use of molecular oxygen as oxidant make this protocol very environmentally friendly and practical.

Figure optionsDownload as PowerPoint slide