Nucleophilic carbenes as organocatalysts.
N-Heterocyclic carbenes (NHC) have become an important class of organocatalysts and class of ligands for transition-metal catalysis. In organocatalyzed umpolung reactions, thiazolium salt-derived NHC have been used successfully for decades. Even so, during recent years there has been an increased interest in NHC-catalyzed transformations and many new reactions have been developed. This article focuses on the use of NHC in the conjugate umpolung of alpha,beta-unsaturated aldehydes.
Glorius
F
F
Organisch Chemisches Institut, Westfälische Wilhelms-Universität Münster, Münster, Germany. glorius@uni-muenster.de
Hirano
K
K
D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D006838:Hydrocarbons; D007097:Imines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009930:Organic Chemicals / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D006838:Hydrocarbons; D007097:Imines; D007659:Ketones; D008024:Ligands; D009930:Organic Chemicals; C030011:carbene; D000171:Acrolein; C012796:2-butenal; D008697:Methane; C012843:cinnamaldehyde