A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone

You Sang Lee, Won Keun Choung, Kyoung Hoon Kim, Tae Won Kang, Deok-Chan Ha

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A key 1-β-methylcarbapenem intermediate is synthesized from a highly diastereoselective condensation between the titanium enolate of 2′-hydroxypropiophenone with 4-acetoxy-β-lactam followed by ozonolysis of the resulting ketone to the carboxylic acid.

Original languageEnglish
Pages (from-to)867-870
Number of pages4
JournalTetrahedron
Volume60
Issue number4
DOIs
Publication statusPublished - 2004 Jan 19

Fingerprint

Hydroxypropiophenone
Lactams
Carboxylic Acids
Titanium
Ketones
Condensation
1 beta-methylcarbapenem
4-hydroxypropiophenone

Keywords

  • Azetidinones
  • Carbapenems
  • Condensation
  • Enolates
  • Ozonolysis
  • Stereoselective

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone. / Lee, You Sang; Choung, Won Keun; Kim, Kyoung Hoon; Kang, Tae Won; Ha, Deok-Chan.

In: Tetrahedron, Vol. 60, No. 4, 19.01.2004, p. 867-870.

Research output: Contribution to journalArticle

Lee, You Sang ; Choung, Won Keun ; Kim, Kyoung Hoon ; Kang, Tae Won ; Ha, Deok-Chan. / A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone. In: Tetrahedron. 2004 ; Vol. 60, No. 4. pp. 867-870.
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