Ｚ‐選択的Ｈｏｒｎｅｒ‐Ｗａｄｓｗｏｒｔｈ‐Ｅｍｍｏｎｓ反応

• 安藤 香織

  琉球大学教育学部

書誌事項

タイトル別名

• Z-Selective Horner-Wadsworth-Emmons Reaction.
• Z センタクテキ Horner Wadsworth Emmons ハンノウ

抄録

The Horner-Wadsworth-Emmons modification of the Wittig reaction is a widely used method for the preparation of α, β-unsaturated esters. The phosphonate anions are strongly nucleophilic and react readily with carbonyl compounds under mild conditions to form olefins and water-soluble phosphate esters in good yields. Since this reaction preferentially gives more stable E-olefins in general, extensive efforts have been devoted to the stereoselective construction of Z -α, β-unsaturated esters. Several attempts have been made by the choice of cation, temperature, and solvent, but they are with a limited success. On the other hand, the special phosphonate reagents including (CF₃CH₂O) ₂P (O) CH₂CO₂Me and (ArO) ₂P (O) CH₂CO₂R gave highly selective routes to a wide range of Z-α, β-unsaturated esters. This review describes these efforts. The mechanism of the HWE reaction is also described briefly.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 58 (9), 869-876, 2000

  公益社団法人 有機合成化学協会

キーワード

• Horner-Wadsworth-Emmons reaction
• Z-selective olefination
• Z-α
• β-unsaturated esters
• phosphonate reagents
• aldehyde
• alkyl (diarylphosphono) acetate
• methyl bis (trifluoroethyl) phosphonoacetate

詳細情報

• CRID: 1390282680255493248
• NII論文ID: 10008821774
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.58.869
• COI: 1:CAS:528:DC%2BD3cXmtlKgt7o%3D
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 5474946
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I5474946
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可