期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 2, 页码 691-695出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409224
关键词
asymmetric catalysis; enantioselectivity; hydrogen bond; oxygenation; ruthenium
资金
- Leverhulme Trust
- Deutsche Forschungsgemeinschaft [Ba1372/17]
- Cluster of Excellence RESOLV [EXC 1069]
Spirocyclic oxindoles undergo an enantioselective oxygenation reaction (nine examples; e.r. up to 97:3) upon catalysis by a chiral ruthenium porphyrin complex (1mol%). The catalyst exhibits a lactam ring, which is responsible for substrate association through hydrogen bonds, and an active ruthenium center, which is in a defined spatial relationship to the oxygenation substrate. DFT calculations illustrate the perfect alignment of the active site with the reactive CH bond and suggestin line with the kinetic isotope effectan oxygen rebound mechanism for the reaction.
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