Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 19, Pages 6519-6523Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600600
Keywords
enantioselectivity; hydrogen bonds; photochemistry; radical reactions; ruthenium
Categories
Funding
- Deutsche Forschungsgemeinschaft [GRK 1626]
- 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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