Organocatalyzed Kinetic Resolution of Racemic Carboxylic Acids

Abstract

The kinetic resolution of racemic compounds is a reliable method to prepare important chiral molecules in highly optically enriched forms. Although methods for the catalytic kinetic resolution of chiral alcohols, amines, and epoxides have been extensively investigated, the kinetic resolution of racemic carboxylic acids has remained under‐developed despite the importance of chiral carboxylic acids. Excellent catalytic approaches for the kinetic resolution of racemic carboxylic acids via esterification using chiral organocatalysts have been reported by several research groups. Furthermore, the organocatalyzed lactonization of alkenyl and alkynyl carboxylic acids has also been adapted to achieve kinetic resolution. Herein, the methods typically used to produce the organocatalyzed kinetic resolution of racemic carboxylic acids are reviewed to elucidate the current status of this research.

X-ray crystallographic structure of a novel enantiopure chiral isothiourea with potential applications in enantioselective synthesis

“…Besides exhibiting catalytic activity in the transfer of acyl groups, chiral isothioureas are also effective catalysts in a variety of other reactions, such as 1,3-dipolar cycloadditions (Hesping et al, 2015;Li et al, 2015), sigmatropic rearrangements (West et al, 2014), [4+2] and [2+2] cycloadditions (Abbasov et al, 2014(Abbasov et al, , 2017Belmessieri et al, 2011;Kim et al, 2023), the kinetic resolution of chiral racemic amides and carboxylic acids (Shiina et al, 2012;Yang et al, 2011Yang et al, , 2012Okuno et al, 2023), and enantioselective silylations (Xu et al, 2015), among others (Sheppard et al, 2011;Liao et al, 2023;Stockhammer et al, 2023).…”