title: Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands.
abstract: 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).
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. biyo@pharm.hokudai.ac.jp
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sato
authors.forename: Yu
authors.initials: Y
authors.lastname: Hinata
authors.forename: Reiko
authors.initials: R
authors.lastname: Seki
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Oonishi
authors.forename: Nozomi
authors.initials: N
authors.lastname: Saito
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008024:Ligands; D009532:Nickel / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006571:Heterocyclic Compounds; D008024:Ligands; D012821:Silanes; D009532:Nickel