期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 20, 页码 6747-6751出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902029
关键词
asymmetric catalysis; C-C activation; palladium; reaction mechanisms; small-ring systems
资金
- National Natural Science Foundation of China [21772051]
- Zhejiang Provincial Natural Science Foundation of China [LY18B020013, LZ18B020001]
A palladium-catalyzed enantioselective intramolecular sigma-bond cross-exchange between C-I and C-C bonds is realized, providing chiral indanones bearing an alkyl iodide group and an all-carbon quaternary stereocenter. Pd/TADDOL-derived phosphoramidite is found to be an efficient catalytic system for both C-C bond cleavage and alkyl iodide reductive elimination. In addition to aryl iodides, aryl bromides can also be used for this transformation in the presence of KI. Density-functional theory (DFT) calculation studies support the ring-opening of cyclobutanones occuring through an oxidative addition/reductive elimination process involving Pd-IV species.
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