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Scientific article
English

Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones

Published inChemistry, vol. 18, no. 28, p. 8731-8747
Publication date2012
Abstract

The copper-catalyzed conjugate addition of various Grignard reagents to polyconjugated enones (dienone and enynone derivatives) is reported. The catalyst system, composed of copper triflate and an NHC ligand, led to the unusual selective formation of the 1,4-addition products. This reaction allows for the creation of all-carbon chiral quaternary centers with enantiomeric excesses up to 99 %. The remaining unsaturation on the 1,4 adducts give access to valuable synthetic transformations.

Keywords
  • Asymmetric synthesis
  • Conjugate additions
  • Copper
  • Grignard reagents
  • N-heterocyclic carbenes
Citation (ISO format)
TISSOT, Matthieu et al. Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones. In: Chemistry, 2012, vol. 18, n° 28, p. 8731–8747. doi: 10.1002/chem.201200502
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ISSN of the journal0947-6539
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Creation07/04/2012 9:02:00 AM
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