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

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

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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 erythro- and threo-β-hydroxyphenylalanines, respectively, via the oxidative cleavage of a furan ring, ring-opening of oxazolidinone, and deprotection.

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