Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 5, Pages 1608-1611Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409572
Keywords
asymmetric catalysis; homologation; scandium; alpha-diazoesters; beta-ketoesters
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Funding
- National Natural Science Foundation of China [210321061, 21290182, 21332003]
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A catalytic asymmetric intramolecular homologation of simple ketones with alpha-diazoesters was firstly accomplished with a chiral N,N'-dioxide-Sc(OTf)(3) complex. This method provides an efficient access to chiral cyclic alpha-aryl/alkyl beta-ketoesters containing an all-carbon quaternary stereocenter. Under mild conditions, a variety of aryl-and alkyl-substituted ketone groups reacted with alpha-diazoester groups smoothly through an intramolecular addition/rearrangement process, producing the beta-ketoesters in high yield and enantiomeric excess.
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