Cationic Cascade Strategy for the Synthesis of Dihydrobenzofuran and Isochromane Scaffolds
Patrycia K Zybura1, Kyla J Grant1, Alison J Frontier1
1Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, United States.
Abstract:
Oxygen heterocycles are valued for their prevalence in bioactive molecules and their metabolic stability. We report a Brønsted-acid-promoted, oxygen-interrupted halo-Prins/halo-Nazarov cascade that enables the stereospecific construction of dihydrobenzofuran and isochromane scaffolds from simple enyne and carbonyl precursors. This approach unites de novo heterocycle construction with late-stage functionalization, providing access to complex oxygen heterocycles of relevance to medicinal chemistry.
Related Concept Videos
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction


![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)