title: Diastereoselective reaction of sulfoxonium ylides, aldehydes and ketenes: an approach to trans-γ-lactones.
abstract: In this paper, a novel approach to γ-lactones from the reaction of sulfoxonium ylides, aldehydes, and ketenes is described. The new ylide-based method provides access to γ-lactones from disubstituted ketenes, in good yields, and with good diastereoselectivity favoring the trans-diastereomer (11 examples with dr ≥ 82:18, dr up to 92:8).
authors.affiliation: Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Mukulesh
authors.initials: M
authors.lastname: Mondal
authors.forename: Han-Jen
authors.initials: HJ
authors.lastname: Ho
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Peraino
authors.forename: Melanie A
authors.initials: MA
authors.lastname: Gary
authors.forename: Kraig A
authors.initials: KA
authors.lastname: Wheeler
authors.forename: Nessan J
authors.initials: NJ
authors.lastname: Kerrigan
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D005030:Ethylenes; D007659:Ketones; D007783:Lactones; D013452:Sulfonium Compounds; C008223:ketene