title: Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation.
abstract: A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally protected syn 1,2-diols were obtained with high levels of diastereocontrol, and these products were selectively deprotected and selectively functionalized into synthetically useful compounds.
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Ignacio
authors.initials: I
authors.lastname: Colomer
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Rosimeire Coura
authors.initials: RC
authors.lastname: Barcelos
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Kirsten E
authors.initials: KE
authors.lastname: Christensen
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe