title: Catalytic asymmetric carbohydroxylation of alkenes by a tandem diboration/Suzuki cross-coupling/oxidation reaction.
abstract: [reaction: see text] Chiral nonsymmetric 1,2-diboron adducts are generated by catalytic enantioselective diboration. Oxidation of these adducts provides 1,2-diols in good yield. Alternatively, 1,2-diboron compounds may be reacted, in situ, with aryl halides wherein the less hindered C-B bond participates in cross-coupling. The remaining C-B bond is then oxidized in the reaction workup thereby allowing for net asymmetric carbohydroxylation of alkenes in a tandem one-pot diboration/Suzuki coupling/oxidation sequence.
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Steven P
authors.initials: SP
authors.lastname: Miller
authors.forename: Jeremy B
authors.initials: JB
authors.lastname: Morgan
authors.forename: Felix J
authors.initials: FJ
authors.lastname: Nepveux
authors.forename: James P
authors.initials: JP
authors.lastname: Morken
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000475:Alkenes; D001896:Boron Compounds