title: Diastereoselective synthesis of γ-lactones through reaction of enediolates with α,β-unsaturated sulfoxonium salts.
abstract: Studies of the reaction of lithium enediolates with α,β-unsaturated sulfoxonium salts are described. γ-Lactones were formed in very good to excellent yields (82% → 99% for 11 examples) and with very good to excellent diastereoselectivity (dr >90:10 for 10 examples), favoring the trans-diastereomer.
authors.affiliation: †Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Peraino
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 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Nessan J
authors.initials: NJ
authors.lastname: Kerrigan
mesh_terms: D003622:Dapsone / Q000031:analogs & derivatives / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D009861:Onium Compounds; D003622:Dapsone; D008094:Lithium