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Updated: Mar 6, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Generation of Polysubstituted Tetrahydrofurans via Urea-Enabled, Pd-Catalyzed Olefin Heteroannulation
Shannon T O'Neil1, Owen E Monteferrante1, Brooke R Stanley1
1Department of Chemistry, University of Rochester, 120 Trustee Road, Rochester, New York 14627, United States.
Abstract:
Herein, we report a palladium-catalyzed heteroannulation approach to couple 2-bromoallyl alcohols and 1,3-dienes to generate a broad range of polysubstituted tetrahydrofuran (THF) rings enabled by urea ligands. Under urea-enabled Pd catalysis, a structurally diverse range of ambiphiles and dienes can be engaged to generate THF products with varying substitution patterns. These products can be readily transformed into prevalent core scaffolds in polyketide natural products.
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