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- Title
Catalytic, Cascade Ring-Opening Benzannulations of 2,3-Dihydrofuran O, O- and N, O-Acetals.
- Authors
Aponte ‐ Guzmán, Joel; Phun, Lien H.; Cavitt, Marchello A.; Taylor, J. Evans; Davy, Jack C.; France, Stefan
- 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.
- Subjects
DIHYDROFURANS; ACETAL resins; RING formation (Chemistry); CHEMICAL reactions; HYDROLYSIS
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 30, p10405
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201601954