7,7'-Dihydroxy-8,8'-biquinolyl (8,8'-diazaBINOL) is an axially chiral polyfunctional heterocyclic analog of the well known ligand 1,1'-bi-2-naphthol (BINOL). 8,8'-DiazaBINOL is readily decorated with ancillary groups and it has a range of applications; however, poor solubility in common organic solvents and modest configurational stability limit its usefulness in enantioselective catalysis. A structural chimera of 8,8'-diazaBINOL and BINOL, 7-hydroxy-8-(2-hydroxynaphthalen-1-yl)quinoline (8-azaBINOL), is envisioned to remedy this situation by offering similar polyfunctionality to 8,8'-diazaBINOL but with other attributes more akin to BINOL. The synthesis, physical properties, resolution, chiroptical properties, and enantiomerization kinetics of 8-azaBINOL will be described and this new member of the azaBINOL family contrasted against the more familiar 8,8'-diazaBINOL and BINOL molecules.

7-Hydroxy-8-(2-hydroxynaphthalen-1-yl)quinoline: A new member of the azaBINOL family with superior configurational stability and solubility to 7,7'-dihydroxy-8,8'-biquinolyl

251st National Meeting (2016)

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