New synthetic routes towards various α-fluorinated aryl ketones and their enantioselective reductions using baker's yeast

Balaka Barkakaty, Yutaka Takaguchi, Sadao Tsuboi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Highly electrophilic dichlorofluoromethyl aryl ketones were obtained by oxidation of dichlorofluoromethyl aryl alcohols. Subsequent dechlorination of these ketones using sodium formaldehyde sulfoxylate (Rongalite) and reductive dehalogenating system SnCl2/Al led to various fluoromethyl aryl ketones and chlorofluoromethyl aryl ketones, respectively. Asymmetric reductions of these fluorinated ketones using the inexpensive baker's yeast produced the corresponding fluoromethyl aryl alcohols with different enantioselectivities.

Original languageEnglish
Pages (from-to)970-976
Number of pages7
JournalTetrahedron
Volume63
Issue number4
DOIs
Publication statusPublished - Jan 22 2007

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Ketones
Yeast
Saccharomyces cerevisiae
Alcohols
Dechlorination
Enantioselectivity
Formaldehyde
Sodium
Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

New synthetic routes towards various α-fluorinated aryl ketones and their enantioselective reductions using baker's yeast. / Barkakaty, Balaka; Takaguchi, Yutaka; Tsuboi, Sadao.

In: Tetrahedron, Vol. 63, No. 4, 22.01.2007, p. 970-976.

Research output: Contribution to journalArticle

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