Complete chiral symmetry breaking of an amino acid derivative directed by circularly polarized light Noorduin, Wim L.; Bode, Arno A.C.; Meijden, Maarten van

By search of a library of closely related structures, two conglomerate imines of the amide of 2-fluorophenylglycine have been discovered and unambiguously characterized. One conglomerate is formed on reaction with benzaldehyde and the other on reaction with 4-Br-benzaldehyde. The crystal structures of both have been determined. Both deracemise on grinding of the crystals under conditions whereby racemisation in solution can occur. Deracemisation of the former compound is hampered both by hydrate formation and formation of a polymorph. In contrast the latter deracemises efficiently. Hydrolysis of the enantiomerically pure (R)-imine to enantiomerically pure (R)-2-fluorophenylglycine proceeds smoothly. Either the (R)- or the (S)-enantiomer of the imine can be produced at will by seeding.