9-anthrylmethoxyacetic acid esterification shifts-correlation with the absolute stereochemistry of secondary alcohols

Assignment of the absolute configuration of a secondary alcohol can be carr ied out by comparison of its proton NMR spectra with that of its ester with 9-anthrylmethoxyacetic acid [(R) or (S)-9AMA]. The esterification shifts o bserved for the two substituents L-1/L-2 of the alcohol depend on their spa tial location with respect to the anthryl group. Identification of the subs tituent that results strongly shielded and of the one not shielded leads to the absolute configuration of the alcohol. Several open and cyclic alcohol s of known absolute stereochemistry have been tested and the scope and limi tations of the method discussed, (C) 1998 Elsevier Science Ltd. All rights reserved.