Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation

Magnus Rueping*, Mirjam Stoeckel, Erli Sugiono, Thomas Theissmann

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

62 Scopus citations

Abstract

A highly enantioselective organocatalytic transfer hydrogenation enabling the synthesis of both 6-fluoro-2-methyltetrahydroquinoline and 7,8-difluoro-3-methyl-benzoxazine has been developed. These key building blocks can for the first time be synthesized using the same methodology allowing fast and efficient, metal-free access to the antibiotic fluoroquinolones flumequine and levofloxacine.

Original languageEnglish (US)
Pages (from-to)6565-6568
Number of pages4
JournalTetrahedron
Volume66
Issue number33
DOIs
StatePublished - Aug 14 2010

Keywords

  • Asymmetric reduction
  • Brønsted acid
  • Flumequine
  • Levofloxacine
  • Organocatalysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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