Preparation of enantiomers of 9-(1-amino-2,2-dimethylpropyl)-9,10-dihydroanthracene. Conformational study and their behaviour as chiral solvating agents

Homochiral forms of 9-(1-amino-2,2-dimethylpropyl)-9,10-dihydroanthracene were prepared by hydrolysis of crystallised diastereomeric salts of mandelic acid. The activity as chiral solvating agent was tested in the presence of several alcohols and acids. A boat conformation of the central ring was demonstrated by NMR studies and MM3 calculations.