Deracemization of Benzoin and its Derivatives via Kinetic, Dynamic Kinetic, Aerobic Oxidative Kinetic, and Reagent-mediated resolution.

Abstract

The production of enantiomerically pure compounds remains a vital and valuable objective in modern organic chemistry due to their broad applications in fields such as biosensing, optics, electronics, photonics, catalysis, nanotechnology, and drug or DNA delivery. Optically pure α-hydroxy ketones, in particular, are key structural components in many drugs and natural products with significant biological activity. Among these, benzoin type α-hydroxy ketones, which possess two adjacent functional groups, a carbonyl and a hydroxy group, are especially important. These functional groups can be easily transformed into the significant organic compounds such as 1,2 amino alcohols and 1,2 diols etc, which are important intermediates for synthesis of high profile biological active natural products. Deracemization of racemic compounds remains one of the most effective strategies for producing optically pure compounds, despite recent advances in asymmetric synthesis. Due to the importance of chiral benzoins, numerous studies have focused on their asymmetric synthesis. At the same time, many research groups have developed various methods for resolving racemic benzoins, including kinetic resolution, dynamic kinetic resolution, metal-catalyzed aerobic oxidative kinetic resolution, and reagent-mediated resolution. In this context, we aim to provide a comprehensive review of the various resolution methods applied specifically to racemic benzoins. To the best of our knowledge, no comprehensive review on the resolution of racemic benzoins has been published to date.