Nucleophilic aromatic substitution of 2-sulfonyl-substituted 1-methoxynaphthalenes with Grignard reagents

Abstract

2-Alkylsulfonyl, -phenoxysulfonyl or -sulfamoyl substituted 1-methoxynaphthalenes 1 undergo nucleophilic displacement of the 1-methoxy group when treated with Grignard reagents; the chiral sulfamoyl-substituted naphthalene 1f on treatment with the 2-methoxy-1-naphthyl Grignard reagent 2d induced axial chirality to give the 1,1′-binaphthyl 3fd in 80% diastereoisomeric excess (de).