Chemo enzymatic synthesis of Rengyol and Isorengyol |
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Authors: | Christoph Kobler |
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Institution: | Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany |
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Abstract: | Cyanohydrins 2 of O-protected 4-hydroxycyclohexanones 1 are excellent starting compounds for the synthesis of Isorengyol (I) and Rengyol (II). The cyano group of the O-benzyl derivative 2d is first converted into the corresponding aldehyde 4, which via Wittig olefination led to the vinyl compound 6. Hydroboration of the trans-derivative (trans-6) leads, after debenzylation, to Isorengyol, whereas hydroboration and debenzylation of the cis-isomer (cis-6) gives Rengyol. With hydroxynitrile lyases (HNLs) as catalysts the stereoselective preparation of cis- as well as trans-cyanohydrin 2d is possible, which enables the selective preparation of Isorengyol or Rengyol, respectively. The trans-configuration of Isorengyol and the cis-configuration of Rengyol were secured by X-ray crystal structure analysis. |
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Keywords: | Rengyol Isorengyol Hydroxynitrile lyase Cyanohydrins cis/trans-Selectivity |
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