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

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.

Key words

asymmetric catalysis - oxazaborolidines - cyclohexen­ones - reduction - desymmetrization

References

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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.