1116086-50-0Relevant articles and documents
Kinetic resolution of racemic α-arylalkanoic acids with achiral alcohols via the asymmetric esterification using carboxylic anhydrides and acyl-transfer catalysts
Shiina, Isamu,Nakata, Kenya,Ono, Keisuke,Onda, Yu-Suke,Itagaki, Makoto
supporting information; experimental part, p. 11629 - 11641 (2010/10/04)
A variety of optically active carboxylic esters are produced by the kinetic resolution of racemic α-substituted carboxylic acids using achiral alcohols, aromatic or aliphatic carboxylic anhydrides, and chiral acyl-transfer catalysts. The combination of 4-methoxybenzoic anhydride (PMBA) or pivalic anhydride with the modified benzotetramisole-type catalyst ((S)-β-Np-BTM) is the most effective for promotion of the enantioselective coupling reaction between racemic carboxylic acids and a novel nucleophile, bis(α-naphthyl) methanol, to give the corresponding esters with high ees. This protocol was successfully applied to the production of nonracemic nonsteroidal anti-inflammatory drugs from racemic compounds utilizing the transacylation process to generate the mixed anhydrides from the acid components with the suitable carboxylic anhydrides.
Kinetic resolution of racemic carboxylic acids using achiral alcohols by the promotion of benzoic anhydrides and tetramisole derivatives: Production of chiral nonsteroidal anti-inflammatory drugs and their esters
Shiina, Isamu,Nakata, Kenya,Onda, Yu-Suke
experimental part, p. 5887 - 5890 (2009/05/27)
A variety of optically active carboxylic esters were produced by kinetic resolution of racemic carboxylic acids by using achiral alcohols, benzoic anhydrides, and Birman's tetramisole-type catalysts. Bis(α-naphthyl) methanol is a very effective reagent for producing the corresponding esters with high ee values in the presence of 4-methoxybenzoic anhydride (PMBA) as the coupling reagent by promotion of benzotetramisole derivatives (BTM, α-Np-BTM, and β-Np-BTM). This protocol directly provides chiral carboxylic esters from free carboxylic acids and achiral alcohols by utilizing a transacylation process to generate the mixed anhydrides from the acid components with benzoic anhydride derivatives in the presence of chiral catalysts. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.