Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 19, Pages 5212-5216Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700105
Keywords
[4+2] annulations; C1 ammonium enolates; cooperative catalysis; copper; heterocycles
Categories
Funding
- NSFC [21232007]
- Chinese Academy of Science [XDB20020000]
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An asymmetric catalytic decarboxylative [4+2] annulation of 4-ethynyl dihydrobenzooxazinones and carboxylic acids has been established by cooperative copper and nucleophilic Lewis base catalysis. A C1 ammonium enolate and copper-allenylidene complex, each catalytically generated from different substrates, underwent a cascade asymmetric propargylation and lactamization process to yield optically active 3,4-dihydroquinolin-2-one derivatives with excellent levels of stereoselectivity (up to 99% ee, 95:5d.r.).
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