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Synthesis 2009(24): 4268-4273  
DOI: 10.1055/s-0029-1217095
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

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
Fax: +49(89)28913315; e-Mail: thorsten.bach@ch.tum.de;
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Publication History

Received 6 October 2009
Publication Date:
03 November 2009 (online)

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Abstract

3-(Silyloxy)oxetanes are obtained by irradiating mixtures of aromatic aldehydes and silyl enol ethers in benzene as the solvent. The reactions occur with high simple diastereoselectivity and, when R¹ is chiral, with high facial diastereoselectivity. Under similar conditions, but in acetonitrile rather than benzene as the preferred solvent, the Paternò-Büchi reaction of N-acyl enamines (enamides) gives the corresponding protected 3-aminooxetanes. The cis-products are obtained with significant simple diastereoselectivity.

Key words

cycloadditions - heterocycles - oxetanes - Paternò-Büchi reactions - photochemistry

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1

Present address: Lummus Novolen GmbH, Gottlieb-Daimler-Str. 8, 68165 Mannheim, Germany.

2

Present address: Boehringer Ingelheim Pharma, Binger Str. 173, 55216 Ingelheim, Germany.