Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 5, Pages 1410-1414Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201309182
Keywords
alkylation; asymmetric catalysis; copper; ligand design; synthetic methods
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Funding
- Dalian Institute of Chemical Physics (CAS)
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The first enantioselective copper-catalyzed decarboxylative propargylic alkylation has been developed. Treatment of propargyl beta-ketoesters with a catalyst, prepared in situ from [Cu(CH3CN)(4)BF4] and a newly developed chiral tridentate ketimine P,N,N-ligand under mild reaction conditions, generates beta-ethynyl ketones in good yields and with high enantioselectivities without requiring the pregeneration of ketone enolates. This new process provides facile access to a range of chiral beta-ethynyl ketones in a highly enantioenriched form.
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