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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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
Volume28
Issue number30
DOIs
Publication statusPublished - 1987
Externally publishedYes

Fingerprint

Carbonyl compounds
Ketones
Pentanones
Metals
Phosphites
Aluminum
Aldehydes
Sodium
Phosphates
3-hydroxybutanal
lithium aluminum hydride
cupric bromide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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. / Kuroboshi, Manabu; Okada, Yoshiji; Ishihara, Takashi; Ando, Teiichi.

In: Tetrahedron Letters, Vol. 28, No. 30, 1987, p. 3501-3504.

Research output: Contribution to journalArticle

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