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
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
Journal ISSN0947-6539
653views
0downloads

Technical informations

Creation04/07/2012 09:02:00
First validation04/07/2012 09:02:00
Update time14/03/2023 17:38:37
Status update14/03/2023 17:38:37
Last indexation29/10/2024 20:23:39
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack