Enantioselective recognition of amines with an atropisomeric 1,8-bisphenolnaphthalene

1,8-Bis[5′(2′-hydroxy-4′-methylbiphenyl)]naphthalene, 2, was prepared from 1,8-dibromonaphthalene and 4-methoxy-2-methylphenylboronic acid in four steps with 51% overall yield. The axially chiral anti-isomer of 2 is stable to racemization at room temperature and the free energy of activation for the conversion of the anti-isomer to the syn-form was determined as 110.0 kJ/mol at 77.1 °C. At submillimolar concentration, enantiopure 2 can be used as circular dichroism sensor to detect a wide range of chiral amines.

The synthesis of an axially chiral 1,8-bisphenolnaphthalene that is stable to racemization at room temperature, readily available in enantiopure form and utilized for enantioselective recognition of chiral amines is described.Figure optionsDownload as PowerPoint slide