Organocatalytic α-hydroxylation or α- aminoxylation of Carbonyl Compounds

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Abstract

SHS investigation development is considered from the geographical and historical viewpoint. 3 stages are described. Within Stage 1 the work was carried out in the Department of the Institute of Chemical Physics in Chernogolovka where the scientific discovery had been made. At Stage 2 the interest to SHS arose in different cities and towns of the former USSR. Within Stage 3 SHS entered the international scene. Now SHS processes and products are being studied in more than 50 countries.

Abstract

α-Hydroxylation or α-aminoxylation of carbonyl compounds in the presence of an organocatalyst has become a significant method for the creation of asymmetric C-O bonds. From the first studies with the classical proline-type or Cinchona-derived organocatalysts, methods have evolved to more efficient systems. Phase-transfer organocatalysts, flow chemistry, ionic liquids, electrochemistry or photo-oxidation permit the reaction with a large range of substrate. While originally aldehydes and ketones were used in these reactions, it is now possible to extend the scope to amides or dicarbonyl compounds such as β-keto ester and β-keto amide. The present review aims to present a general overview of the evolution of these systems.

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