Tetrahedron

Imino 1, 2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone

O Miyata, T Koizumi, H Asai, R Iba, T Naito

Index: Miyata, Okiko; Koizumi, Tomoko; Asai, Hiroshi; Iba, Ryuichi; Naito, Takeaki Tetrahedron, 2004 , vol. 60, # 17 p. 3893 - 3914

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Citation Number: 44

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 ...

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