ABSTRACT
The biscarbazole murrastifoline-F and the naphthylisoquinoline ancisheynine present very rare natural N,C-bonded biaryls. Furthermore, such compounds are used as reagents and catalysts in asymmetric synthesis. The synthesis of the optically pure axially chiral biaryls by the intramolecular coupling with the use of chiral tether is often the result of oxidative coupling reaction. Atroposelective intramolecular oxidative coupling reaction also allows to synthesize natural compounds belonging to the lignans group. Generally, the coupling of aryl Grignard compounds with chirally modified alkoxyarenes or aryl sulfoxides leads to axially chiral biaryls, wherein as the chiral leaving group (R)-menthol is often used. The oxidative coupling of phenols allows to obtain intermediate compounds in the synthesis of natural alkaloids belonging to the Erythrina family, the morphine derivatives, and the natural precursor of bisnaphthopyrone, nigerone. In the case of nonbridged biaryl compounds, atropisomerism depends on the presence of bulky substituents next to the axis, whereas bridged biaryls should have the rigid and long chains of rings.
