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Synthesis 2006(16): 2643-2645
DOI: 10.1055/s-2006-942484
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
Weitere Informationen
Received
9 March 2006
Publikationsdatum:
12. Juli 2006 (online)
Publikationsverlauf
Publikationsdatum:
12. Juli 2006 (online)
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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
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References
The absolute configuration of diversonol has not yet been determined.
14This 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.