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: thorsten.bach
ch.tum.de
F. Vogt, K. Jödicke, J. Schröder, T. Bach, Synthesis, 2009, 4268-4273.
DOI: 10.1055/s-0029-1217095
Abstract
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
