title: N-Heterocyclic Carbene-Catalyzed δ-Carbon LUMO Activation of Unsaturated Aldehydes.
abstract: An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β-γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote δ-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.
authors.affiliation: †Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
authors.forename: Tingshun
authors.initials: T
authors.lastname: Zhu
authors.affiliation: †Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
authors.forename: Chengli
authors.initials: C
authors.lastname: Mou
authors.forename: Baosheng
authors.initials: B
authors.lastname: Li
authors.forename: Marie
authors.initials: M
authors.lastname: Smetankova
authors.affiliation: †Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
authors.forename: Bao-An
authors.initials: BA
authors.lastname: Song
authors.affiliation: †Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
authors.forename: Yonggui Robin
authors.initials: YR
authors.lastname: Chi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001555:Benzene Derivatives; D001572:Benzofurans; D006571:Heterocyclic Compounds; C030011:carbene; D002244:Carbon; C082022:phthalide; D008697:Methane