An Efficient Protocol for the Enantioselective Preparation of a Key Polyfunctionalized Cyclohexane. New Access to (R)- and (S)-4-Hydroxy-2-cyclohexenone and (R)- and (S)-trans-Cyclohex-2-ene-1,4-diol
Starting from very accessible raw materials such as p-methoxyphenol, ethylene glycol, and thiophenol, a protocol has been developed to prepare multigram quantities of the polyfunctionalized cyclohexane (±)-7. A highly efficient resolution of (±)-7 has been achieved through enantioselective acetylati...
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Veröffentlicht in: | Journal of organic chemistry 2008-05, Vol.73 (9), p.3486-3491 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Starting from very accessible raw materials such as p-methoxyphenol, ethylene glycol, and thiophenol, a protocol has been developed to prepare multigram quantities of the polyfunctionalized cyclohexane (±)-7. A highly efficient resolution of (±)-7 has been achieved through enantioselective acetylation catalyzed by Candida antarctica lipase B. Straightforward and enantioselective syntheses of 4-hydroxy-2-cyclohexenone, 1, trans-cyclohex-2-ene-1,4-diol, 2, and their O-protected derivatives 18 and 19 have been readily accomplished from 7. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo800107h |