Application of a novel chromophoric reagent, 2,2′-binaphthyl-3,3′-dicarbonyl cyanide, to the absolute configuration determination of chiral secondary alcohols

Abstract

2,2′-Binaphthyl-3,3′-dicarbonyl cyanide possessing two reaction sites was designed and synthesized as a new chromophoric reagent for exciton-coupled circular dichroism (ECCD), which is more effective in determination of the absolute stereochemistry of the target chiral alcohols than 2,2′-binaphthyl-3-methoxycarbonyl-3′-carbonyl cyanide, which contains only one reaction site. The CD spectra of the 2,2′-binaphthyl diesters derived from chiral secondary alcohols show bisignate curves centered at 240 nm, of which the Δε value was roughly twice as large as that of the binaphthyl methyl monoester.