Axially chiral phenolic derivatives of 8,8-biquinolyl and 8-(naphth-1-yl)quinoline as platforms for discovery: The unfolding story of the 'azaBINOLs'

This account encapsulates the Author's interests in the chemistry of nitrogenous analogs of 1,1'-bi-2-naphthol (BINOL) in which either the 8-position ('8-azaBINOL') or both of the 8- and 8'-positions ('8,8'-diazaBINOL') of the binaphthyl have been formally replaced by N-atoms. The consequences that such structural perturbations have on various kinetic (rate of enantiomerization), thermodynamic (basicity), and biological (anti-HIV activity) properties of the biaryl nucleus are elaborated and opportunities for the application of azaBINOLs in reaction catalysis are highlighted. The synthesis of parent azaBINOLs and their substituted derivatives is summarized, together with techniques to resolve these axially chiral compounds into their enantiomeric atropisomers. [GRAPHICS] .