title: Highly chemo-, enantio-, and regioselective synthesis of α,α-disubstituted furanones by Cu-catalyzed conjugate addition.
abstract: A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported. The Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place. Synthetic transformations of furanones represent facile approaches to various cyclic or acyclic compounds bearing a quaternary stereogenic center.
authors.affiliation: Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan); PRESTO (Japan) Science and Technology Agency (JST), 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012 (Japan). kendo@se.kanazawa-u.ac.jp.
authors.forename: Kohei
authors.initials: K
authors.lastname: Endo
authors.forename: Sayuri
authors.initials: S
authors.lastname: Yakeishi
authors.forename: Ryotaro
authors.initials: R
authors.lastname: Takayama
authors.forename: Takanori
authors.initials: T
authors.lastname: Shibata
mesh_terms: D000535:Aluminum / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007783:Lactones; D009942:Organometallic Compounds; D003300:Copper; D000535:Aluminum
keywords: addition reactions; aluminum; asymmetric synthesis; copper; heterocyclic compounds