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ChemInform Abstract: Synthesis of α-Fluoro-β-hydroxy Alkylsulfanyl Esters via a Nucleophilic Fluorination of Sulfides.

✍ Scribed by C. JOUEN; S. LEMAITRE; T. LEQUEUX; J. C. POMMELET

Publisher
John Wiley and Sons
Year
2010
Weight
40 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

1998 hydroxycarboxylic acids

hydroxycarboxylic acids (ether carboxylic acids) and esters (benzene compounds) Q 0450

50 -104

Synthesis of α-Fluoro-β-hydroxy Alkylsulfanyl Esters via a Nucleophilic Fluorination of Sulfides.

-An efficient synthesis of 2-alkylsulfanyl-2-fluoro esters by halogen exchange reaction using NEt 3 •3HF as a fluoride source is developed. Enolates derived from these esters add to carbonyl compounds to furnish separable diastereomeric mixtures of the title compounds. In the case of benzaldehyde, the selectivity of this addition can be controlled by the reaction temperature. The investigation is presented with a view to developing novel fluorine-containing enzyme inhibitors. - (JOUEN,

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