Behavior of the 9-Anthryl-tert-butylcarbinol as a Chiral Solvating Agent. Study of Diastereochemical Association by Intermolecular NOE and Molecular Dynamics Calculations

The 9-anthryl- tert -butylcarbinol was tested as a chiral solvating agent (CSA) in the presence of racemic forms of mentil- p -toluenesulfinate, 9-(1-amino-2,2-dimethylpropyl)-9,19-dihydroanthracene, α-methoxyphenylacetic acid and 1-phenyl-1,2-ethanediol. Diastereomeric complexes were found to form between each enantiomer of these last two compounds. One of the enantiomers of 9-anthryl- tert -butylcarbinol was studied by means of intermolecular NOE and molecular dynamics calculations. Major thermodynamic and structural differences were found.