Cationic Cascade Strategy for the Synthesis of Dihydrobenzofuran and Isochromane Scaffolds
Patrycia K. Zybura, Kyla J. Grant, Alison J. Frontier
TL;DR
A new chemical method creates complex oxygen-containing ring structures important for drug development.
Contribution
A stereospecific cascade reaction for synthesizing dihydrobenzofuran and isochromane scaffolds using enyne and carbonyl precursors.
Findings
A Brønsted-acid-promoted cascade reaction enables the synthesis of oxygen heterocycles.
The method allows de novo construction of dihydrobenzofuran and isochromane scaffolds.
Late-stage functionalization is achieved alongside heterocycle formation.
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.
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Taxonomy
TopicsSynthetic Organic Chemistry Methods · Catalytic Alkyne Reactions · Catalytic C–H Functionalization Methods