Brønsted Acid‐Catalyzed Enantioselective and Para‐Selective Addition of Phenols to 1‐Alkynylnaphth‐2‐Ols

Abstract A chiral Brønsted acid‐catalyzed synthesis of axially chiral alkenes was developed via an enantioselective and para ‐selective Friedel–Crafts reaction between phenols and 1‐alkynylnaphth‐2‐ols. This methodology features an efficient hydroarylation with high functional group tolerance, complete para ‐selectivity, excellent yields (up to 99%), and enantioselectivities (up to 94% ee) in the presence of a N ‐triflylphosphoramide catalyst. DFT calculations were performed to investigate para ‐selectivity and results indicate that both kinetics and thermodynamics parameters are more favorable compared to ortho ‐selectivity.