Synthesis 2006(16): 2643-2645  
DOI: 10.1055/s-2006-942484
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Short and Practical Access to both Enantiomers of 4-Hydroxycyclohexenone Based on a Desymmetrizing CBS Reduction

Carl F. Nising, Ulrike K. Ohnemüller, Stefan Bräse*
Institut für Organische Chemie, Universität Karlsruhe, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)6088581; e-Mail: braese@ioc.uka.de;
Further Information

Publication History

Received 9 March 2006
Publication Date:
12 July 2006 (eFirst)

Abstract

By employing an unprecedented CBS-catalyzed reductive desymmetrization of the readily available meso-diketone 2, both enantiomers of the cyclohexenone precursor 3 can be synthesized in up to 92% yield and 98% ee. From this precursor, 4-hydro­xy­cyclohexenone (1) is easily liberated by a retro Diels-Alder reaction.

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9

The absolute configuration of diversonol has not yet been determined.

14

This observation might be due to the fact that (R)- and (S)-Me-CBS were received from different suppliers and is being currently investigated in our group.