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

Research output: Contribution to journalArticle

106 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)5291-5294
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number41
DOIs
Publication statusPublished - 1988
Externally publishedYes

Fingerprint

Amino Sugars
Imines
Acetals
Derivatives
Esters
2-azetidinone
difluoroacetic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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

In: Tetrahedron Letters, Vol. 29, No. 41, 1988, p. 5291-5294.

Research output: Contribution to journalArticle

Taguchi, Takeo ; Kitagawa, Osamu ; Suda, Yoshimitsu ; Ohkawa, Shinji ; Hashimoto, Akihiro ; Iitaka, Yohichi ; Kobayashi, Yoshiro. / 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. In: Tetrahedron Letters. 1988 ; Vol. 29, No. 41. pp. 5291-5294.
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abstract = "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).",
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AU - Taguchi, Takeo

AU - Kitagawa, Osamu

AU - Suda, Yoshimitsu

AU - Ohkawa, Shinji

AU - Hashimoto, Akihiro

AU - Iitaka, Yohichi

AU - Kobayashi, Yoshiro

PY - 1988

Y1 - 1988

N2 - 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).

AB - 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).

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