889765-30-4Relevant academic research and scientific papers
Studies on gold(i) and gold(iii) alcohol functionalised NHC complexes
Jónsson, Helgi Freyr,Orthaber, Andreas,Fiksdahl, Anne
, p. 5128 - 5138 (2021/04/26)
Five pairs of novel chiral alcohol functionalised gold(i) and gold(iii) NHC complexes derived from chiral amino alcohols, were synthesized and characterised (NMR, IR, HRMS). Single crystal X-ray diffraction data of gold(i) and gold(iii) complexes are reported and discussed. The chiral imidazolium preligands were readily synthesizedviathe oxalamides, subsequent reduction and final orthoformate condensation. An improved method was used for generation of gold(i) NHC complexes (up to 92%) and further oxidation afforded the corresponding gold(iii) NHC complexes (up to 99%). All the Au(i) and Au(iii) NHC complexes proved far more catalytically active in a 1,6-enyne alkoxycyclization test reaction than our previously testedN,N- andP,N-ligated Au(iii) complexes. Comparative gold(i) and gold(iii) catalytic studies demonstrated different catalytic ability, depending on the NHC ligand flexibility and bulkiness. Excellent yields (92-99%) of target alkoxycyclization product were obtained with both gold(i) and gold(iii) complexes with the bulkyN1-Mes-N2-ethanol based NHC ligand.
Design, synthesis, and organocatalytic activity of n-heterocyclic carbenes functionalized with hydrogen-bond donors in enantioselective reactions of homoenolates
Nawaz, Faisal,Zaghouani, Mehdi,Bonne, Damien,Chuzel, Olivier,Rodriguez, Jean,Coquerel, Yoann
, p. 8253 - 8264 (2014/01/06)
A focused library of chiral imidazolinium salts functionalized with urea-type hydrogen-bond donor moieties has been prepared from the chiral pool. The corresponding N-heterocyclic carbenes were evaluated as organocatalysts in three enantioselective reacti
Design and synthesis of new bidentate alkoxy-NHC ligands for enantioselective copper-catalyzed conjugate addition
Clavier, Hervé,Coutable, Ludovic,Toupet, Lo?c,Guillemin, Jean-Claude,Mauduit, Marc
, p. 5237 - 5254 (2007/10/03)
A new family of chiral alkoxy-N-heterocyclic carbene (NHC) ligands has been designed for the enantioselective copper-catalyzed conjugate addition of dialkylzincs to enones. These new bidentate NHC ligands were synthesized in high overall yields using a five-step procedure starting from commercially available β-aminoalcohols. Influence of the temperature, base, solvent and copper source were studied in order to optimize the stereoselectivity of the addition. High reactivity and excellent enantioselectivity were obtained at ambient temperature with a range of cyclic enones and dialkylzinc. Addition to acyclic enones has also been studied.
New bidentate alkoxy-NHC ligands for enantioselective copper-catalysed conjugate addition
Clavier, Herve,Coutable, Ludovic,Guillemin, Jean-Claude,Mauduit, Marc
, p. 921 - 924 (2007/10/03)
Chiral alkoxy-imidazolinium salts are easily available via a five-step procedure starting from β-aminoalcohols. This new family of alkoxy-N-heterocyclic carbene (NHC) precursors is shown to be highly active in the enantioselective copper-catalysed conjugate addition to cyclic enones. Complete conversion with low catalyst loading and good enantiomeric excesses up to 93% were obtained at room temperature.
