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Synlett 1997; 1997(1): 91-92
DOI: 10.1055/s-1997-688
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Efficient Synthesis of Isotopically Pure [18O]-Epoxides using Molecular Oxygen

Michael Schöttler, Wilhelm Boland*
  • *Institut für Organische Chemie und Biochemie, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany, Fax: +49 (0)228 735388; E-mail: Boland@uni-bonn.de
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Publication Date:
22 March 2004 (online)

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High yields of isotopically pure [18O]-epoxides are obtained from alkenes and 18O2 gas in the presence of isobutyraldehyde (Kaneda epoxidation). Unlike peracids, the system allows the selective epoxidation of the double bond in a keto-alkene without competing Baeyer-Villiger oxidation of the carbonyl group.

Kaneda-epoxidation - [18O]-oxiranes - [18O]-5,6-epoxycholesterol - [18O]-epoxides of fatty acids - [18O]-epoxyjasmonate