Synthesis, resolution and absolute configuration determination of (S)- and (R)-4-formyl-5-hydroxy [2.2]paracyclophane and its application in the asymmetric synthesis of α-amino acids

Abstract

Racemic (R,S)-4-formyl-5-hydroxy[2.2]paracyclophane (FHPC) was resolved into enantiomers via its Schiff's base with (S)- and (R)-α-phenylethylamine (α-PEAM) and its absolute configuration was determined by an X-ray diffraction structural study. Scalemic FHPC or its derivatives can be used as chiral auxiliaries for the asymmetric synthesis of β-hydroxy-α-amino acids and α-methylphenylalanine with ees ranging mostly from 45 to 98%.