Microwave-Assisted Synthesis of (+/-)-Mandelic Acid-d(5), Optical Resolution, and Absolute Configuration Determination

作者:Bruno Claudio; Lentini Giovanni*; Lovece Angelo; Cavalluzzi Maria Maddalena; Carocci Alessia; Catalano Alessia; Franchini Carlo
来源:Journal of Chemistry, 2013, 2013: 386238.
DOI:10.1155/2013/386238

摘要

An efficient microwave-assisted synthesis of (+/-)-mandelic acid-d(5) was developed. The racemic mixture was resolved by diastereomeric salt formation using 1-phenylethylamine enantiomers as resolving agents. At each step, the resolution process was checked by determining mandelic acid-d(5) enantiomer ee values directly on fractional crystalized diastereomeric salts by chiral capillary electrophoresis analysis. Highly enriched (-)- and (+)-mandelic acid-d(5) (95% and 90% ee, resp.) were obtained and their absolute configurations-R and S, respectively-were determined by correlation of the (-)-mandelic acid-d(5) circular dichroism spectrum to the (R)-mandelic acid one.

  • 出版日期2013