Macrocyclic amides consisting of helical chiral 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylate

Helical chiral 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid was synthesized and resolved in multigram quantities. The absolute configuratio n was determined by X-ray analysis of the bis(camphorsultamamide) derivativ e. A series of optically active macrocyclic amides consisting of the chiral unit and a dianiline spacer were synthesized by one-pot procedures, and th eir structures were compared by spectroscopy and X-ray crystallography. One of the cycloamides exhibited catalytic activity in the asymmetric addition of diethylzinc to aromatic aldehydes. N-Alkylated derivatives were also sy nthesized, which possessed folded structures distinct from those of the par ent cyclic amides.