A new efficient method for the generation of F-alkyl ketone metal enolates by using copper(II) bromide-lithium aluminium hydride reagent and their aldol reaction with carbonyl compounds

Manabu Kuroboshi, Yoshiji Okada, Takashi Ishihara, Teiichi Ando

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1-Substituted F-1-alkenyl phosphates, readily prepared from F-alkyl ketones and sodium diethyl phosphite, were treated with copper(II) bromide-lithium aluminium hydride reagent at -30 °C to generate in situ F-alkyl ketone aluminium enolates, which underwent the aldol reaction with various aldehydes to give the corresponding α-fluoro-α-F-alkyl β-hydroxy ketones in fairly good to excellent yields.

Original languageEnglish
Pages (from-to)3501-3504
Number of pages4
JournalTetrahedron Letters
Issue number30
Publication statusPublished - 1987
Externally publishedYes


ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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