{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T12:26:42Z","timestamp":1785932802325,"version":"3.56.0"},"reference-count":39,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2022,4,14]],"date-time":"2022-04-14T00:00:00Z","timestamp":1649894400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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, \u03b1,\u03b2-unsaturated ketones, esters (cis- and trans-), and amides (cis- and trans-). The reaction mechanism is discussed.<\/jats:p>","DOI":"10.3390\/molecules27082538","type":"journal-article","created":{"date-parts":[[2022,4,19]],"date-time":"2022-04-19T01:03:01Z","timestamp":1650330181000},"page":"2538","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes"],"prefix":"10.3390","volume":"27","author":[{"given":"Varvara A.","family":"Drozd","sequence":"first","affiliation":[{"name":"Boreskov Institute of Catalysis, Pr. Lavrentieva 5, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3035-5828","authenticated-orcid":false,"given":"Roman V.","family":"Ottenbacher","sequence":"additional","affiliation":[{"name":"Boreskov Institute of Catalysis, Pr. Lavrentieva 5, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7009-8950","authenticated-orcid":false,"given":"Konstantin P.","family":"Bryliakov","sequence":"additional","affiliation":[{"name":"Boreskov Institute of Catalysis, Pr. Lavrentieva 5, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,4,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Ojima, I. (2010). Asymmetric Oxidations and Related Reactions. Catalytic Asymmetric Synthesis, John Wiley & Sons. [3rd ed.].","DOI":"10.1002\/9780470584248"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Bryliakov, K.P. (2014). Environmentally Sustainable Catalytic asymmetric Oxidations, CRC Press.","DOI":"10.1201\/b17422"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1143","DOI":"10.2174\/1385272821666170221151356","article-title":"Applications of Chiral Three-membered Rings for Total Synthesis: A Review","volume":"21","author":"Dalpozzo","year":"2017","journal-title":"Curr. Org. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1681","DOI":"10.1021\/cr200073d","article-title":"Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis","volume":"112","author":"Thibodeaux","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1039\/c2np00078d","article-title":"Electrophilic and nucleophilic enzymatic cascade reactions in biosynthesis","volume":"29","author":"Ueberbacher","year":"2012","journal-title":"Nat. Prod. Rep."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2004","DOI":"10.1002\/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5","article-title":"Click Chemistry: Diverse Chemical Function from a Few Good Reactions","volume":"40","author":"Kolb","year":"2001","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1038\/nature07371","article-title":"Biologically inspired oxidation catalysis","volume":"455","author":"Que","year":"2008","journal-title":"Nature"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1722","DOI":"10.1039\/C0CS00077A","article-title":"Recent advances in catalytic asymmetric epoxidation using the environmentally benign oxidant hydrogen peroxide and its derivatives","volume":"40","author":"Ilyashenko","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3030","DOI":"10.1016\/j.ccr.2013.05.010","article-title":"Metal Catalyzed Asymmetric Sulfoxidation, Epoxidation and Hydroxylation by Hydrogen Peroxide","volume":"257","author":"Srour","year":"2013","journal-title":"Coord. Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"e6217","DOI":"10.1002\/aoc.6217","article-title":"Recent advances and trends in the biomimetic iron-catalyzed asymmetric epoxidation","volume":"35","author":"Radhika","year":"2021","journal-title":"Appl. Organomet. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"11406","DOI":"10.1021\/acs.chemrev.7b00167","article-title":"Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H2O2 and O2","volume":"117","author":"Bryliakov","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1002\/tcr.201700032","article-title":"Chiral Manganese Aminopyridine Complexes: The Versatile Catalysts of Chemo- and Stereoselective Oxidations with H2O2","volume":"18","author":"Ottenbacher","year":"2018","journal-title":"Chem. Rec."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"8611","DOI":"10.1021\/acscatal.0c02073","article-title":"Rational Design of Bioinspired Catalysts for Selective Oxidations","volume":"10","author":"Vicens","year":"2020","journal-title":"ACS Catal."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1272","DOI":"10.1002\/adsc.202001073","article-title":"Recent Trends and Prospects in Homogeneous Manganese-Catalysed Epoxidation","volume":"363","author":"Philip","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"213443","DOI":"10.1016\/j.ccr.2020.213443","article-title":"Artificial nonheme iron and manganese oxygenases for enantioselective olefin epoxidation and alkane hydroxylation reactions","volume":"421","author":"Chen","year":"2020","journal-title":"Coord. Chem. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3622","DOI":"10.1021\/ol901400m","article-title":"Asymmetric Epoxidation of Olefins with Chiral Bioinspired Manganese Complexes","volume":"11","author":"Wu","year":"2009","journal-title":"Org. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"6750","DOI":"10.1002\/chem.201103802","article-title":"Manganese Catalysts with C1-Symmetric N4 Ligand for Enantioselective Epoxidation of Olefins","volume":"18","author":"Wang","year":"2012","journal-title":"Chem. Eur. J."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/j.jorganchem.2012.03.034","article-title":"Non-heme manganese complexes of C1-symmetric N4 ligands: Synthesis, characterization and asymmetric epoxidations of \u03b1,\u03b2-enones","volume":"715","author":"Wang","year":"2012","journal-title":"J. Organomet. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5777","DOI":"10.1002\/ejic.201402663","article-title":"A Mononuclear Manganese Complex of a Tetradentate Nitrogen Ligand\u2014Synthesis, Characterizations, and Application in the Asymmetric Epoxidation of Olefins","volume":"2014","author":"Shen","year":"2014","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"372","DOI":"10.1021\/acs.orglett.5b03309","article-title":"Enantioselective Epoxidation of Olefins with H2O2 Catalyzed by Bioinspired Aminopyridine Manganese Complexes","volume":"18","author":"Shen","year":"2016","journal-title":"Org. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4528","DOI":"10.1021\/acscatal.8b00874","article-title":"Mechanistic Insights into the Enantioselective Epoxidation of Olefins by Bioinspired Manganese Complexes: Role of Carboxylic Acid and Nature of Active Oxidant","volume":"8","author":"Du","year":"2018","journal-title":"ACS Catal."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"11857","DOI":"10.1021\/acscatal.0c02634","article-title":"Effect of Ligand Topology on the Reactivity of Chiral Tetradentate Aminopyridine Manganese Complexes","volume":"10","author":"Lin","year":"2020","journal-title":"ACS Catal."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1002\/adsc.202101151","article-title":"Asymmetric Epoxidation of Olefins Catalyzed by Substituted Aminobenzimidazole Manganese Complexes Derived from L-Proline","volume":"364","author":"Tian","year":"2022","journal-title":"Adv. Synth. Catal."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1002\/adsc.201100409","article-title":"Stereoselective Epoxidation of Alkenes with Hydrogen Peroxide using a Bipyrrolidine-Based Family of Manganese Complexes","volume":"354","author":"Gomez","year":"2012","journal-title":"Adv. Synth. Catal."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"6158","DOI":"10.1021\/ol403018x","article-title":"Highly Stereoselective Epoxidation with H2O2 Catalyzed by Electron-Rich Aminopyridine Manganese Catalysts","volume":"15","author":"Cusso","year":"2013","journal-title":"Org. Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2430","DOI":"10.1021\/acs.orglett.9b00729","article-title":"Enantioselective Epoxidation of \u03b2,\u03b2-Disubstituted Enamides with a Manganese Catalyst and Aqueous Hydrogen Peroxide","volume":"21","author":"Claraso","year":"2019","journal-title":"Org. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"e202114932","DOI":"10.1002\/anie.202114932","article-title":"Remote Amino Acid Recognition Enables Effective Hydrogen Peroxide Activation at a Manganese Oxidation Catalyst","volume":"61","author":"Vicens","year":"2022","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"885","DOI":"10.1002\/adsc.201100030","article-title":"Non-Heme Manganese Complexes Catalyzed Asymmetric Epoxidation of Olefins by Peracetic Acid and Hydrogen Peroxide","volume":"353","author":"Ottenbacher","year":"2011","journal-title":"Adv. Synth. Catal."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1196","DOI":"10.1021\/cs300205n","article-title":"Asymmetric Epoxidations with H2O2 on Fe and Mn Aminopyridine Catalysts: Probing the Nature of Active Species by Combined Electron Paramagnetic Resonance and Enantioselectivity Study","volume":"2","author":"Lyakin","year":"2012","journal-title":"ACS Catal."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1599","DOI":"10.1021\/cs500333c","article-title":"Highly Enantioselective Bioinspired Epoxidation of Electron-Deficient Olefins with H2O2 on Aminopyridine Mn Catalysts","volume":"4","author":"Ottenbacher","year":"2014","journal-title":"ACS Catal."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"979","DOI":"10.1021\/acscatal.5b02299","article-title":"Enantioselective Epoxidations of Olefins with Various Oxidants on Bioinspired Mn Complexes: Evidence for Different Mechanisms and Chiral Additive Amplification","volume":"6","author":"Ottenbacher","year":"2016","journal-title":"ACS Catal."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2778","DOI":"10.1002\/adsc.202100198","article-title":"Manganese Catalyzed Enantioselective Epoxidation of \u03b1,\u03b2-Unsaturated Amides with H2O2","volume":"363","author":"Ottenbacher","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2535","DOI":"10.1002\/adsc.201700541","article-title":"Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines","volume":"359","author":"Chen","year":"2017","journal-title":"Adv. Synth. Catal."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"208","DOI":"10.1039\/C3CY00528C","article-title":"Manganese complexes with non-porphyrin N4 ligands as recyclable catalyst for the asymmetric epoxidation of olefins","volume":"4","author":"Maity","year":"2014","journal-title":"Catal. Sci. Technol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"4138","DOI":"10.1021\/ol401812h","article-title":"Asymmetric Epoxidation of Alkenes Catalyzed by a Porphyrin-Inspired Manganese Complex","volume":"15","author":"Dai","year":"2013","journal-title":"Org. Lett."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"13101","DOI":"10.1039\/D0CC04440G","article-title":"Ligand regulation for manganese-catalyzed enantioselective epoxidation of olefins without acid","volume":"56","author":"Xu","year":"2020","journal-title":"Chem. Commun."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"6145","DOI":"10.1016\/0040-4020(95)00304-Q","article-title":"Sodium perborate and sodium percarbonate: Cheap, safe and versatile oxidising agents for organic synthesis","volume":"51","author":"McKillop","year":"1995","journal-title":"Tetrahedron"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"665","DOI":"10.1246\/cl.1986.665","article-title":"\u201cSodium percarbonate\u201d (SPC) as a hydrogen peroxide source for organic synthesis","volume":"15","author":"Ando","year":"1986","journal-title":"Chem. Lett."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1021\/ol047836h","article-title":"Asymmetric Epoxidation of cis-Alkenes Mediated by Iminium Salts:\u2009 Highly Enantioselective Synthesis of Levcromakalim","volume":"7","author":"Page","year":"2005","journal-title":"Org. Lett."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/8\/2538\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T22:54:12Z","timestamp":1760136852000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/8\/2538"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,14]]},"references-count":39,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2022,4]]}},"alternative-id":["molecules27082538"],"URL":"https:\/\/doi.org\/10.3390\/molecules27082538","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,4,14]]}}}