Efficient synthesis of enantiomerically and diastereomerically pure [2.2]paracyclophane-based N,O-ligands

Efficient syntheses of different enantiomerically and diastereomerically pure N,O-ligands with alkylamino and phenol groups attached to the [2.2]paracyclophane framework are described. Several transformations of the ortho-lithiated [2.2]paracyclophan-4-yl diethylcarbamate 7 and the reduction of the [2.2]paracyclophane imino derivatives 3, 4, 17, 18, and 21 allow the preparation of a wide range of compounds in which the chiral environment can be controlled by the planar chiral fragment and modified by the presence of one or two additional chiral centers in the alkylamino group.