title: Opening of substituted oxetanes with H(2)O(2) and alkyl hydroperoxides: stereoselective approach to 3-peroxyalcohols and 1,2,4-trioxepanes.
abstract: [reaction: see text] Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.
authors.affiliation: Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA. pdussault1@unl.edu
authors.forename: Patrick H
authors.initials: PH
authors.lastname: Dussault
authors.forename: Tony K
authors.initials: TK
authors.lastname: Trullinger
authors.forename: Farhana
authors.initials: F
authors.lastname: Noor-e-Ain
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis; D004148:Dioxolanes / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000962:Antimalarials; D004148:Dioxolanes; D004988:Ethers, Cyclic; D010545:Peroxides; C005287:oxetane