title: Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals.
abstract: An unprecedented N-heterocyclic carbene (NHC)-catalyzed annulation of enals to form 3,4-disubstituted cyclopentanones has been discovered. Aryl enals undergo dimerization in the presence of a single-electron oxidant to form C2 symmetric cyclopentanones. A cross-reaction has also been developed, allowing for the synthesis of differentially substituted cyclopentanones. Mechanistically, the reaction is thought to proceed through radical intermediates, further establishing the synthetic utility of this class of reactivity.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: White
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D006571:Heterocyclic Compounds; C007201:cyclopentanone; C030011:carbene; D008697:Methane