Intermolecular enantioselective dearomatization reaction of β-naphthol using meso-aziridine: a bifunctional in situ generated magnesium catalyst

Abstract

A direct, facile, and highly diastereo- and enantioselective dearomatization reaction of β-naphthol derivatives with aziridines has been developed for the first time. A newly designed Box-OH ligand was employed for an in situ generated magnesium catalyst and proved to be efficient. The corresponding dearomatization product was transformed into a polycyclic scaffold and polyhydroxylated compound. (1) H NMR studies revealed the activation mode of the dearomatization process of β-naphthols, and a clear positive nonlinear effect was observed in the reaction, and provides insight into the coordination environment around the Mg(II) center and the possible active species.

Keywords: arenes; aromaticity; intermolecular reactions; ligand design; magnesium.