title: Catalytic, Cascade Ring-Opening Benzannulations of 2,3-Dihydrofuran O,O- and N,O-Acetals.
abstract: An Al(OTf)3 -catalyzed intramolecular cascade ring-opening benzannulation of 2,3-dihydrofuran O,O- and N,O-acetals is described. The cascade sequence involves the dihydrofuran ring-opening by acetal hydrolysis, an intramolecular Prins-type cyclization, and aromatization to generate an array of benzo-fused (hetero)aromatic systems in up to 95 % yield. This method represents the first example of dihydrofuran acetal usage in benzannulation reactions. The approach provides excellent regiocontrol based on the choice of alkenes used to form the requisite dihydrofuran acetals.
authors.affiliation: School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA.
authors.forename: Joel
authors.initials: J
authors.lastname: Aponte-Guzmán
authors.affiliation: School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA.
authors.forename: Lien H
authors.initials: LH
authors.lastname: Phun
authors.affiliation: School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA.
authors.forename: Marchello A
authors.initials: MA
authors.lastname: Cavitt
authors.affiliation: School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA.
authors.forename: J Evans
authors.initials: JE
authors.lastname: Taylor
authors.affiliation: School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA.
authors.forename: Jack C
authors.initials: JC
authors.lastname: Davy
authors.affiliation: Petit Institute for Bioengineering and Bioscience, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA. stefan.france@chemistry.gatech.edu.|School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA. stefan.france@chemistry.gatech.edu.
authors.forename: Stefan
authors.identifier: http://orcid.org/0000-0001-5998-6167
authors.initials: S
authors.lastname: France
keywords: benzannulation; domino reactions; fused-ring systems; heterocycles; ring-opening cyclizations