Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands.
Nickel(0)-catalyzed asymmetric three-component coupling of 1,3-dienes, aldehydes, and silanes has been realized utilizing a chiral N-heterocyclic carbene as a ligand. On the basis of the screening of various NHC precursors, an imidazolium salt having 1-(2,4,6-trimethylphenyl)propyl groups on the nitrogen was designed and synthesized. In this reaction, various coupling products were produced in good yields with high regio-, diastereo- (anti selective in the case of the internal 1,3-diene), and enantioselectivities (up to 97% ee).
Sato
Yoshihiro
Y
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. biyo@pharm.hokudai.ac.jp
Hinata
Yu
Y
Seki
Reiko
R
Oonishi
Yoshihiro
Y
Saito
Nozomi
N
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008024:Ligands; D009532:Nickel / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D006571:Heterocyclic Compounds; D008024:Ligands; D012821:Silanes; D009532:Nickel