A new chiral selector based on trans-acenaphthen-1,2-dicarboxylic acid

The chiral selectors (R,R)- and (S,S)-trans-acenaphthen-1,2-dicarboxylic acid bis-allylamide have been synthesized and characterized. The route to the selectors involved synthesis of the trans-dicarboxylic acid via sodiation and carbonation of acenaphthylene, followed by reaction of the bis-acid chloride with allylamine. The racemic bis-allylamide derivative was resolved into its enantiomers by preparative liquid chromatography. The chiral discrimination effect from the (R,R)-selector in the 1H-NMR spectra of a mixture of the enantiomers of O,O'-dibenzoyltartaric acid was studied as a function of temperature. Due to certain ambiguities in the literature concerning the absolute configuration of the (+)-rotating trans-acenaphthen-1,2-dicarboxylic acid, its brucine salt was subjected to X-ray crystallography. This showed the (+)-form to be of (R,R)-configuration.