Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes. 2022

Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
Boreskov Institute of Catalysis, Pr. Lavrentieva 5, 630090 Novosibirsk, Russia.

Asymmetric epoxidation of a series of olefinic substrates with sodium percarbonate oxidant in the presence of homogeneous catalysts based on Mn complexes with bis-amino-bis-pyridine ligands is reported. Sodium percarbonate is a readily available and environmentally benign oxidant that is studied in these reactions for the first time. The epoxidation proceeded with good to high yields (up to 100%) and high enantioselectivities (up to 99% ee) using as low as 0.2 mol. % catalyst loadings. The epoxidation protocol is suitable for various types of substrates, including unfunctionalized alkenes, α,β-unsaturated ketones, esters (cis- and trans-), and amides (cis- and trans-). The reaction mechanism is discussed.

UI MeSH Term Description Entries
D008345 Manganese A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035)
D011725 Pyridines Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D002254 Carbonates Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed) Carbonate
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D004852 Epoxy Compounds Organic compounds that include a cyclic ether with three ring atoms in their structure. They are commonly used as precursors for POLYMERS such as EPOXY RESINS. Epoxide,Epoxides,Epoxy Compound,Oxiranes,Compound, Epoxy,Compounds, Epoxy
D000475 Alkenes Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408) Alkene,Olefin,Olefins,Pentene,Pentenes
D016877 Oxidants Electron-accepting molecules in chemical reactions in which electrons are transferred from one molecule to another (OXIDATION-REDUCTION). Oxidant,Oxidizing Agent,Oxidizing Agents,Agent, Oxidizing,Agents, Oxidizing

Related Publications

Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
August 2009, Organic letters,
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
February 2016, Organic letters,
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
May 2009, The Journal of organic chemistry,
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
December 1997, Inorganic chemistry,
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
July 2014, The Journal of organic chemistry,
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
January 2007, Angewandte Chemie (International ed. in English),
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
August 2013, Organic letters,
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
November 2020, Chemical communications (Cambridge, England),
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
September 2008, Chemical reviews,
Varvara A Drozd, and Roman V Ottenbacher, and Konstantin P Bryliakov
August 2012, Angewandte Chemie (International ed. in English),
Copied contents to your clipboard!