4.6 Article

Enantioselective Visible-Light-Induced Radical-Addition Reactions to 3-Alkylidene Indolin-2-ones

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 19, 页码 6519-6523

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600600

关键词

enantioselectivity; hydrogen bonds; photochemistry; radical reactions; ruthenium

资金

  1. Deutsche Forschungsgemeinschaft [GRK 1626]
  2. Fonds der Chemischen Industrie

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The title compounds underwent a facile and high-yielding addition reaction (19examples, 66-99% yield) with various N-(trimethylsilyl)methyl-substituted amines upon irradiation with visible light and catalysis by a metal complex. If the alkylidene substituent is non-symmetric and if the reaction is performed in the presence of a chiral hydrogen-bonding template, products are obtained with significant enantioselectivity (58-72% ee) as a mixture of diastereoisomers. Mechanistic studies suggest a closed catalytic cycle for the photoactive metal complex. However, the silyl transfer from the amine occurs not only to the product, but also to the substrate, and interferes with the desired chirality transfer.

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