{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,24]],"date-time":"2026-07-24T01:13:06Z","timestamp":1784855586086,"version":"3.55.0"},"reference-count":45,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2009,4,6]],"date-time":"2009-04-06T00:00:00Z","timestamp":1238976000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2009,5,18]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:bold>Get selective!<\/jats:bold> A selective oxidation of 1,2\u2010diols to \u03b1\u2010hydroxyketones catalyzed by organotin compounds has been developed (see scheme). Invaluable chemo\u2010 and stereoselectivity were found in the reaction. The catalytic system has been achieved by electrochemical and chemical oxidation.<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p><jats:p>Electrochemical oxidation of 1,2\u2010diols with a catalytic amount of an organotin compound and a bromide ion as mediators has been developed. Various cyclic and acyclic 1,2\u2010diols were oxidized into the corresponding \u03b1\u2010hydroxyketones in good to excellent yields without C\uf8ffC bond cleavage. Also, oxidation with the use of chemical oxidants was accomplished in the presence of a catalytic amount of an organotin compound. These reactions could discriminate 1,2\u2010diols from isolated hydoxyl groups or 1,3\u2010diols. In the case of a conformationally restricted cyclic 1,2\u2010diol, the axial hydroxyl group was oxidized exclusively. Mono\u2010, di\u2010, and trialkylated tin compounds were examined as mediators and dialkylated tin compounds showed higher catalytic activity than mono\u2010 and trisubstituted ones. Me<jats:sub>2<\/jats:sub>SnCl<jats:sub>2<\/jats:sub> was found to be the most suitable mediator for the selective oxidation.<\/jats:p>","DOI":"10.1002\/chem.200900159","type":"journal-article","created":{"date-parts":[[2009,4,6]],"date-time":"2009-04-06T10:02:49Z","timestamp":1239012169000},"page":"5364-5370","source":"Crossref","is-referenced-by-count":41,"title":["Efficient Oxidation of 1,2\u2010Diols into \u03b1\u2010Hydroxyketones Catalyzed by Organotin 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