Asymmetric synthesis of γ-perfluoroalkyl(aryl) butyrolactones via organoboranes

P. Veeraraghavan Ramachandran, Kamlesh J. Padiya, Vivek Rauniyar, M. Venkat Ram Reddy, Herbert C. Brown

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

Asymmetric 'allyl'boration of fluorinated aldehydes with α-pinene-based 'allyl' boranes provides the corresponding homoallylic alcohols in high ee and de, which upon hydroboration, followed by oxidation with TPAP/NMO furnish γ-perfluoroalkyl(aryl)-γ-butyrolactones.

Original languageEnglish (US)
Pages (from-to)1015-1017
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number5
DOIs
StatePublished - Jan 26 2004

Bibliographical note

Funding Information:
Financial support from the Herbert C. Brown Center for Borane Research 20 and the Aldrich Chemical Company is greatfully acknowledged.

Keywords

  • Allylboration
  • Fluorolactones
  • Homoallylic alcohol
  • Hydroboration
  • α-Pinene

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