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

Balaka Barkakaty; Yutaka Takaguchi; Sadao Tsuboi

doi:10.1016/j.tet.2006.11.019

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 journal › Article › peer-review

20 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 language	English
Pages (from-to)	970-976
Number of pages	7
Journal	Tetrahedron
Volume	63
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2006.11.019
Publication status	Published - Jan 22 2007

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.11.019

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AU - Tsuboi, Sadao

PY - 2007/1/22

Y1 - 2007/1/22

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AB - 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.

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

Abstract

ASJC Scopus subject areas

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