title: Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: enhancement of catalytic efficiency through bifunctional additives.
abstract: An asymmetric intermolecular Stetter reaction of enals with nitroalkenes catalyzed by chiral N-heterocyclic carbenes has been developed. The reaction rate and efficiency are profoundly impacted by the presence of catechol. The reaction proceeds with high selectivities and affords good yields of the Stetter product. Internal redox products were not observed despite of the protic conditions. The impact of catechol has been found to be general, facilitating far lower catalyst loadings than were previously achievable.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Daniel A
authors.initials: DA
authors.lastname: DiRocco
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002396:Catechols / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009574:Nitro Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000475:Alkenes; D002396:Catechols; D006571:Heterocyclic Compounds; D009574:Nitro Compounds; C030011:carbene; C034221:catechol; D008697:Methane