Volume 39, Issue 13 pp. 2302-2304
Communication

Enantioselective Intramolecular [2+2]-Photocycloaddition Reactions in Solution

Thorsten Bach Prof. Dr.

Thorsten Bach Prof. Dr.

Fachbereich Chemie der Philipps-Universität Hans-Meerwein-Strasse, 35032 Marburg (Germany)

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Hermann Bergmann Dipl.-Chem.

Hermann Bergmann Dipl.-Chem.

Fachbereich Chemie der Philipps-Universität Hans-Meerwein-Strasse, 35032 Marburg (Germany)

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Klaus Harms Dr.

Klaus Harms Dr.

Fachbereich Chemie der Philipps-Universität Hans-Meerwein-Strasse, 35032 Marburg (Germany)

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This project was supported by the Deutsche Forschungsgemeinschaft (Ba 1372-4/1 and -4/2) and by the Fonds der Chemischen Industrie. We would like to thank Stefan Sieber (undergraduate research participant) for skillful technical assistance.

Crystal structure determination

Graphical Abstract

Hydrogen bonds facilitate the coordination of prochiral 2-quinolones, such as 1, to the chiral host 2. As a result, the intramolecular [2+2]-photocycloaddition reaction which yields cyclobutanes, such as 3, proceeds with high enantioselectivity (up to 93 % ee). The host can be separated from the products and is recovered almost quantitatively.

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