Enantiomerically Pure (R)‐ and (S)‐15‐Hydroxy[2.2]paracyclophane‐4‐carbaldehyde (iso‐FHPC): A Novel Parent Compound for Planar Chiral Ligands

The planar chiral 15‐hydroxy[2.2]paracyclophane‐4‐carbaldehyde (2, iso‐FHPC) was synthesized and resolved via its Schiff bases 8 by using the enantiomers of α‐phenylethylamine. The absolute configurations of the enantiomers of 2 were determined by a combined X‐ray diffraction and chemical correlation study. Derivatives 9, the first representatives of cyclophane‐derived aminophenols with a pseudo‐gem arrangement of the functional groups were synthesized. All new chiral compounds can be regarded as prospective ligands for asymmetric synthesis and catalysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)