Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 11, Pages 2953-2957Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712340
Keywords
enantioselectivity; hydrogen bonds; manganese; oxygenation; porphyrinoids
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Funding
- Deutsche Forschungsgemeinschaft [Ba 1372-17]
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A chiral manganese porphyrin complex with a two-point hydrogen-bonding site was prepared and probed in catalytic C-H oxygenation reactions of 3,4-dihydroquinolones. The desired oxygenation occurred with perfect site selectivity at the C4 methylene group and with high enantioselectivity in favor of the respective 4S-configured secondary alcohols (12 examples, 29-97% conversion, 19-68% yield, 87-99% ee). Mechanistic studies support the hypothesis that the reaction proceeds through a rate-and selectivity-determining attack of the reactive manganese oxo complex at the hydrogen-bound substrate and an oxygen transfer by a rebound mechanism.
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