Synthesis and characterization of novel chiral derivatizing agents containing β-keto-anthracene adducts (KAAs) by 1H-NMR: aromatic influence and chiral alcohol absolute configuration determination

Abstract

New alternative chiral derivatizing agents, β-keto-anthracene adducts (KAAs), were accomplished and the influence of aromatic moieties at the α-carbon position for elucidation of the absolute configuration of chiral secondary alcohols via NMR was studied. The α-benzoyl substituted KAAs strongly enhance the anisotropic effect which produced greater Δδ^RS values than other conventional reagents. We propose a simplified model to describe the conformations and to assign the absolute configuration in several chiral alcohol samples.