A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate

Yoshio Ito, Takeo Kawabata, Shiro Terashima

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A highly efficient synthesis of the title compound was accomplished employing the addition of diketene to chiral imine as a key stereoselective reaction and using inexpensive (S)-ethy1 lactate as a starting material.

Original languageEnglish
Pages (from-to)5751-5754
Number of pages4
JournalTetrahedron Letters
Volume27
Issue number47
DOIs
Publication statusPublished - Jan 1 1986
Externally publishedYes

Fingerprint

Carbapenems
Imines
Lactic Acid
diketene
ethyl lactate
2-azetidinone

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate. / Ito, Yoshio; Kawabata, Takeo; Terashima, Shiro.

In: Tetrahedron Letters, Vol. 27, No. 47, 01.01.1986, p. 5751-5754.

Research output: Contribution to journalArticle

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