Using the nature of the achiral solvent to orient chiral resolution

Abstract

We demonstrate the unprecedented phenomenon of solvent-oriented resolution of 1,1′-bi-2-naphtol (Binol). Using a resolution agent of a fixed handedness (R,R)-N,N′-dimethyl-1,2-diphenylethane-1,2-diamine (DADPE), we are able to resolve either the (S)- or (R)-enantiomer of Binol by a mere change of the achiral solvent.