title: Alkene anti-Dihydroxylation with Malonoyl Peroxides.
abstract: Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
authors.forename: Carla
authors.initials: C
authors.lastname: Alamillo-Ferrer
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
authors.forename: Stuart C
authors.initials: SC
authors.lastname: Davidson
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Rawling
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.|GlaxoSmithKline Medicines Research Centre , Gunnels Wood Road, Stevenage SG1 2NY, United Kingdom.
authors.forename: Natalie H
authors.initials: NH
authors.lastname: Theodoulou
authors.affiliation: GlaxoSmithKline Medicines Research Centre , Gunnels Wood Road, Stevenage SG1 2NY, United Kingdom.
authors.forename: Matthew
authors.initials: M
authors.lastname: Campbell
authors.affiliation: GlaxoSmithKline Medicines Research Centre , Gunnels Wood Road, Stevenage SG1 2NY, United Kingdom.
authors.forename: Philip G
authors.initials: PG
authors.lastname: Humphreys
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
authors.forename: Alan R
authors.initials: AR
authors.lastname: Kennedy
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
authors.forename: Nicholas C O
authors.initials: NC
authors.lastname: Tomkinson
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry; D007202:Indicators and Reagents; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D010545:Peroxides / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000475:Alkenes; D001688:Biological Products; D007202:Indicators and Reagents; D008314:Malonates; D010545:Peroxides