21196-51-0Relevant articles and documents
Resolution of (±)-Bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic Acid: Crystal Structure of Its Cinchoninium Salt
Jiménez, Lissette,González, Teresa,Brice?o, Alexander,Agrifoglio, Giuseppe,Pastrán, Jesús,Dorta, Romano
, p. 203 - 207 (2016/05/02)
Abstract: Single crystals of (+)-cinchoninium (+)-bicyclo[2.2.1]hept-5-ene-trans-2-carboxyl-3-carboxylate (S,S)-2 were obtained upon resolution of racemic (±)-bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic acid rac-1 with (+)-cinchonine. An X ray diffraction analysis established the most important secondary interactions between the ions that are deemed responsible for the diastereomeric separation process. From (S,S)-2 enantiomerically pure (+)-bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic acid (S,S)-1 was isolated in 72 % yield. Graphical Abstract: An X-ray diffraction analysis of (+)-cinchoninium (+)-bicyclo[2.2.1]hept-5-ene-trans-2-carboxyl-3-carboxylate (S,S)-2 established the most important secondary interactions between the ions that are deemed responsible for the diastereomeric separation process.[Figure not available: see fulltext.]
