Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of <i>N</i>-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins
نویسندگان
چکیده
A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins is reported. The reactions proceed via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate nitrogen-centered radical. Strain-induced ring opening intermolecular addition olefin intermediate carbon-centered radical that reduced anion prior 5-exo cyclization. This enables diastereoselective construction trans-cyclopentanes possessing synthetically useful functional groups.
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2021
ISSN: ['1523-7060', '1523-7052']
DOI: https://doi.org/10.1021/acs.orglett.1c00711