title: Asymmetric Synthesis of γ-Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts.
abstract: A chiral Koga amine-controlled asymmetric synthesis of cis-γ-lactones through a formal [3 + 2] cycloaddition of enediolates with α,β-unsaturated sulfoxonium salts is described. The desired structural motif was formed in moderate to good yields (50-71% for 13 examples), with good to very good diastereoselectivity (dr 5:1 to 10:1 for 20 examples), favoring the cis-isomer, and good to excellent enantioselectivity (70-91% ee for 13 examples).
authors.affiliation: Department of Chemistry, Oakland University , 2200 N. Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Peraino
authors.affiliation: Department of Chemistry, Oakland University , 2200 N. Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Sven H
authors.initials: SH
authors.lastname: Kaster
authors.affiliation: Department of Chemistry, Eastern Illinois University , 600 Lincoln Avenue, Charleston, Illinois 61920-3099, United States.
authors.forename: Kraig A
authors.initials: KA
authors.lastname: Wheeler
authors.affiliation: Department of Chemistry, Oakland University , 2200 N. Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Nessan J
authors.identifier: 0000-0003-3643-5260
authors.initials: NJ
authors.lastname: Kerrigan
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D061565:Cycloaddition Reaction; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000085:Acetates; D000588:Amines; D007783:Lactones; D012492:Salts; D013452:Sulfonium Compounds