Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 22, Pages 6907-6914Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200694
Keywords
arylboronic acids; cuparenone; Michael addition; palladium; quaternary stereocenters
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Funding
- CatchBio Program [053.70.206]
- Netherlands Ministry of Economic Affairs
- Netherlands Ministry of Education, Culture and Science
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An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of beta,beta-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF6, and provides products in up to 99?% enantiomeric excess, with good yields. Based on this strategy, (-)-a-cuparenone has been prepared in only two steps.
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