Chemical and pharmaceutical bulletin

Stereoselective Synthesis of. BETA.-Hydroxyphenylalanines Using Imino 1, 2-Wittig Rearrangement of Hydroximates

O Miyata, H Asai, T Naito

Index: Miyata, Okiko; Asai, Hiroshi; Naito, Takeaki Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 4 p. 355 - 360

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Citation Number: 6

Abstract

The imino 1, 2-Wittig rearrangement of hydroximates containing a furan ring provides a novel method for the synthesis of β-hydroxy-α-amino acids. Upon treatment with LDA, hydroximates smoothly underwent the rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into both cis-and trans-oxazolidinones with high stereoselectivity. The cis-and trans-oxazolidinones were stereoselectively converted into ...