Open AccessMicrowave‐Assisted Synthesis of (±)‐Mandelic Acid‐d5, Optical Resolution, and Absolute Configuration Determination
Author(s) -
Claudio Bruno,
Giovanni Lentini,
Angelo Lovece,
Maria Maddalena Cavalluzzi,
Alessia Carocci,
Alessia Catalano,
Carlo Franchini
Publication year - 2012
Publication title -
journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.436
H-Index - 50
eISSN - 2090-9063
pISSN - 2090-9071
DOI - 10.1155/2013/386238
Subject(s) - mandelic acid , chemistry , diastereomer , enantiomer , absolute configuration , resolution (logic) , enantiomeric excess , circular dichroism , capillary electrophoresis , chromatography , chiral resolution , analytical chemistry (journal) , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science
An efficient microwave-assisted synthesis of (±)-mandelic acid-d5 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-d5 enantiomer ee values directly on fractional crystallized diastereomeric salts by chiral capillary electrophoresis analysis. Highly enriched (−)- and (+)-mandelic acid-d5 (95% and 90% ee, resp.) were obtained and their absolute configurations—R and S, respectively—were determined by correlation of the (−)-mandelic acid-d5 circular dichroism spectrum to the (R)-mandelic acid one
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom