6533b872fe1ef96bd12d2ca8

RESEARCH PRODUCT

Organocatalytic enantioselective aza-Friedel–Crafts reaction of 2-naphthols with benzoxathiazine 2,2-dioxides

Marc Montesinos-magranerGonzalo BlayCarlos VilaRuben CantonM. Carmen MuñozIsabel FernándezJosé R. Pedro

subject

chemistry.chemical_compoundNucleophileChemistryGeneral Chemical EngineeringEnantioselective synthesisOrganic chemistryGeneral ChemistrySesamolFriedel–Crafts reactionBifunctional catalyst

description

An organocatalytic enantioselective aza-Friedel–Crafts addition of 2-naphthols to benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional catalyst. The method allows the use of a wide range of aromatic compounds as nucleophiles, including 1-naphthol and sesamol, and benzoxathiazines 2,2-dioxides, expanding the existing state of the art enantioselective synthesis of aminomethylnaphthol derivatives.

https://doi.org/10.1039/c5ra11168d