Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-quinones: Platform Molecules for Diversity-oriented Synthesis of Biaryldiols.

BINOL is the most representative atropisomer and has been widely used as catalyst and ligand in asymmetric catalysis. A myriad of catalytic asymmetric tools have been elegantly developed for the construction of BINOL and its C 2 -symmetrical derivatives possessing distinct features. Here we present a class of novel axially chiral aryl- p -quinones as platform molecules for the synthesis of non- C 2 symmetric biaryldiols. Two sets of aryl- p -quinone frameworks were synthesized with remarkable enantiocontrol by means of chiral phosphoric acid catalyzed enantioselective arylation of p -quinones via central-to-axial chirality transfer and a wide spectrum of highly functionalized non- C 2 symmetric biaryldiols were obtained with excellent enantiopurity retention.