Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion

Enantiodivergent one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source. A domino organocatalyst-mediated enantioselective Michael reaction and aldol condensation provided centrally chiral dihydronaphthalenes with excellent enantioselectivity, from which an enantiodivergent chirality conversion from central-to-axial chirality was achieved. Both enantiomers of biaryls were obtained with excellent enantioselectivity. All transformations can be conducted in a single reaction vessel. A plausible reaction mechanism for the enantiodivergence is proposed.

Automated summary

A one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source, allowing for an enantiodivergent chirality conversion from central-to-axial chirality with excellent enantioselectivity. Both enantiomers of biaryls were obtained in a single reaction vessel, with a proposed plausible reaction mechanism for the enantiodivergence.