Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate

Vijaya Lingam Manthati, A. Sai Krishna Murthy, Frédéric Caijo, Delphine Drouin, Philippe Lesot, Danielle Grée, René Grée

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's >95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules.

Original languageEnglish (US)
Pages (from-to)2306-2310
Number of pages5
JournalTetrahedron Asymmetry
Volume17
Issue number15
DOIs
StatePublished - Sep 11 2006

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Manthati, V. L., Sai Krishna Murthy, A., Caijo, F., Drouin, D., Lesot, P., Grée, D., & Grée, R. (2006). Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate. Tetrahedron Asymmetry, 17(15), 2306-2310. https://doi.org/10.1016/j.tetasy.2006.08.010