Synthesis of 3,3-difluoro-2-azetidinones and 2,3-dideoxy-2,2-difluoro-3-amino-sugars through the reformatsky reaction of difluoroacetate with imine

Takeo Taguchi, Osamu Kitagawa, Yoshimitsu Suda, Shinji Ohkawa, Akihiro Hashimoto, Yohichi Iitaka, Yoshiro Kobayashi

研究成果査読

112 被引用数 (Scopus)

抄録

The Reformatsky reaction of iodo- or bromodifluoroacetate with imine(5) gave the corresponding 3,3-difluoro-2-azetidinone derivative(1). Reaction of 2,2-difluoroketene silyl acetal(4) with the imine(5a) or N,O-acetal derivatives(8, 9) gave the 3-amino-2,2-difluoro esters. 2,2-Difluoro analogs of 2,3-dideoxy-3-aminosugars(2) including daunosamine derivative (2a) were efficiently prepared through the reaction of 3 or 4 with N-benzylimine of 4-deoxy-L-threose acetonide(5a) and (R)-glyceraldehyde acetonide(5b).

本文言語English
ページ(範囲)5291-5294
ページ数4
ジャーナルTetrahedron Letters
29
41
DOI
出版ステータスPublished - 1988
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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