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

• Miyata Okiko

  Kobe Pharmaceutical University

• Asai Hiroshi

  Kobe Pharmaceutical University

• Naito Takeaki

  Kobe Pharmaceutical University

Bibliographic Information

Other Title

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

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

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 53 (4), 355-360, 2005

  The Pharmaceutical Society of Japan

Keywords

• imino Wittig rearrangement
• hydroximate
• imidate
• amino acid
• oxime ether

Details

• CRID: 1390282679146424192
• NII Article ID: 10016652841
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.53.355
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 7292000
• PubMed: 15802831
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I7292000
• Web Site: http://www.jstage.jst.go.jp/article/cpb/53/4/53_4_355/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• Abstract License Flag: Disallowed