A Simple Access to 2-Epoxy Alcohols: Titanium(IV)-Catalyzed Oxygen Transfer from Allylic Hydroperoxides


  • This work was supported by the Deutsche Forschungsgemeinschaft (Sonderforschungsbereich 172: Molekulare Mechanismen kanzerogener Primärveränderungen), the Stiftung Volkswagenwerk, and the Fonds der Chemischen Industrie.


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A host of new, synthetically valuable 2-epoxy alcohols 3 should be accessible by the generally applicable title reaction. Oxygen transfer from 1 does not proceed intramolecularly; the first step is the formation of the allylic alcohol 2, which is epoxidized in a rapid secondary step by 1 to the product 3. At the same time, compound 2 is reformed.