title: Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H(2)O(2).
abstract: A practical method for the multigram scale selective cis-dihydroxylation of electron deficient alkenes such as diethyl fumarate and N-alkyl and N-aryl-maleimides using H(2)O(2) is described. High turnovers (>1000) can be achieved with this efficient manganese based catalyst system, prepared in situ from a manganese salt, pyridine-2-carboxylic acid, a ketone and a base, under ambient conditions. Under optimized conditions, for diethyl fumarate at least 1000 turnovers could be achieved with only 1.5 equiv. of H(2)O(2) with d/l-diethyl tartrate (cis-diol product) as the sole product. For electron rich alkenes, such as cis-cyclooctene, this catalyst provides for efficient epoxidation.
authors: Stratingh Institute for Chemistry, Faculty of Mathematics and Natural Sciences, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
authors: Pattama
authors: P
authors: Saisaha
authors: Dirk
authors: D
authors: Pijper
authors: Ruben P
authors: RP
authors: van Summeren
authors: Rob
authors: R
authors: Hoen
authors: Christian
authors: C
authors: Smit
authors: Johannes W
authors: JW
authors: de Boer
authors: Ronald
authors: R
authors: Hage
authors: Paul L
authors: PL
authors: Alsters
authors: Ben L
authors: BL
authors: Feringa
authors: Wesley R
authors: WR
authors: Browne
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D005650:Fumarates / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry*; D006900:Hydroxylation; D008301:Maleimides / Q000737:chemistry; D008345:Manganese / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D005650:Fumarates; D008301:Maleimides; D008345:Manganese; C035088:diethyl fumarate; D006861:Hydrogen Peroxide