title: Diaminocyclopropenylidene organocatalysts: beyond N-heterocyclic carbenes.
abstract: Cyclopropenylidene carbenes have been found to be efficient catalysts for the intermolecular Stetter reaction between aromatic aldehydes and α,β-unsaturated ketones. In this transformation, the cyclopropenylidene proved superior to more traditional thiazolium- and triazolium-derived carbenes. Preparation and evaluation of a chiral analogue have also been reported.
authors.affiliation: Trinity Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin 2 (Ireland). connons@tcd.ie.
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Connon
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D003521:Cyclopropanes; D006571:Heterocyclic Compounds; D007659:Ketones; C555684:cyclopropenylidene; C030011:carbene; D009584:Nitrogen; D008697:Methane
keywords: Stetter reaction; asymmetric catalysis; carbenes; cyclopropenylidenes; umpolung