New Applications of the CD Exciton Chirality Method. Stereochemical Assignment of Organic Compounds Containing Carboxylic Acid Groups

Abstract

CD exciton chirality methods are described for the stereochemical assignment of organic compounds containing carboxylic acid groups. Using the chromophoric combination 2-naphthoate or 2-anthroate and 9-anthrylmethyl group the absolute stereochemistry of α- and β-hydroxy carboxylic acids can be deduced from a single CD measurement. Furthermore, as demonstrated with cyclic and acylic dicarboxylic acids, the direct esterification of sterically hindered carboxyl groups with 2-naphthol also allows the stereochemical assignment via CD spectroscopy.