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Scientific article
English

Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones

Published inChemistry, vol. 16, no. 32, p. 9890-9904
Publication date2010
Abstract

The copper-catalyzed conjugate addition of Grignard reagents to 3-substituted cyclic enones allows the formation of all-carbon chiral quaternary centers. We demonstrate in this article that N-heterocyclic carbenes act as efficient chiral ligands for this transformation. High enantioselectivities (up to 96 % ee) could be obtained for a variety of substrates.

Keywords
  • Asymmetry
  • Conjugate addition
  • Copper
  • Grignard reaction
  • N-heterocyclic carbenes
Citation (ISO format)
KEHRLI, Stefan et al. Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones. In: Chemistry, 2010, vol. 16, n° 32, p. 9890–9904. doi: 10.1002/chem.201000471
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Article (Published version)
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Identifiers
ISSN of the journal0947-6539
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Creation09/30/2010 11:14:00 AM
First validation09/30/2010 11:14:00 AM
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