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Paternò-Büchi Reactions of Silyl Enol Ethers and Enamides

Florian Vogt, Kai Jödicke, Jürgen Schröder, Thorsten Bach*

*Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany, Email:

F. Vogt, K. Jödicke, J. Schröder, T. Bach, Synthesis, 2009, 4268-4273.

DOI: 10.1055/s-0029-1217095


3-(Silyloxy)oxetanes are obtained by irradiating mixtures of aromatic aldehydes and silyl enol ethers in benzene as the solvent. Under similar conditions, but in acetonitrile rather than benzene, the Paternò-Büchi reaction of N-acyl enamines gives the corresponding protected 3-aminooxetanes. The reactions occur with high diastereoselectivity.

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Key Words

cycloadditions, heterocycles, oxetanes, Paternò-Büchi reaction, photochemistry

ID: J66-Y2009-3720