Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone |
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Authors: | Okiko Miyata |
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Institution: | Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan |
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Abstract: | The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone. |
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Keywords: | Imino Wittig rearrangement Hydroximate Imidate Oxime ether Cytoxazone |
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