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Enantioselective Copper-Catalyzed Three-Component Cascade Boronation-Dearomatization Reaction: Synthesis of Chiral Boron-Containing 1,4-Dihydropyridines.

A three-component cascade boronation-dearomatization reaction of alkenes, a diboron compound, and a pyridinium salt is diclosed, affording chiral boron-containing 1,4-dihyropyridines in high yields (≤98%) and diastereoselectivity (≤10:1 dr), along with… Click to show full abstract

A three-component cascade boronation-dearomatization reaction of alkenes, a diboron compound, and a pyridinium salt is diclosed, affording chiral boron-containing 1,4-dihyropyridines in high yields (≤98%) and diastereoselectivity (≤10:1 dr), along with excellent enantioselectivity (typically >99% ee). The catalytic system performs efficiently at low catalyst loadings (1 mol %) and was tested with >50 examples, including some biologically active molecules.

Keywords: boronation dearomatization; three component; dearomatization reaction; component cascade; cascade boronation; chiral boron

Journal Title: Organic letters
Year Published: 2025

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