Regioselective Synthesis of α-Perfluoroalkylated Ketals via Double Michael Addition of Alcohols to Activated Alkynes

Ella Ndong; Guy Judicael; Jean Luc Parrain; Mohamed Abarbri

doi:10.1055/s-0034-1380753

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(17): 2635-2640
DOI: 10.1055/s-0034-1380753

paper

Regioselective Synthesis of α-Perfluoroalkylated Ketals via Double Michael Addition of Alcohols to Activated Alkynes

Ella Ndong

^aLaboratoire d’Infectiologie et Santé Publique (UMR 1282), Equipe Recherche et Innovation en Chimie Médicinale, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France eMail: mohamed.abarbri@univ-tours.fr

,

Guy Judicael

^aLaboratoire d’Infectiologie et Santé Publique (UMR 1282), Equipe Recherche et Innovation en Chimie Médicinale, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France eMail: mohamed.abarbri@univ-tours.fr

,

Jean Luc Parrain

^bAix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France

,

Mohamed Abarbri*

^aLaboratoire d’Infectiologie et Santé Publique (UMR 1282), Equipe Recherche et Innovation en Chimie Médicinale, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France eMail: mohamed.abarbri@univ-tours.fr

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Abstract

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Abstract

An efficient method was developed for the synthesis of alkyl 3,3-dialkoxy-3-(perfluoroalkyl)propanoates from ethyl 3-(perfluoroalkyl)propynoates and alcohols using a base-catalyzed double Michael addition reaction (which was accompanied by transesterification in the case of MeOH, EtOH, PrOH, and BuOH). This method provides easy access to the product α-perfluoroalkyl ketals with reasonable to good yields with total regioselectivity. This procedure does not require the use of expensive supplementary additives for the preparation of α-perfluoroalkyl ketals which are very sensitive to acidic conditions.

Key words

hydroalkoxylation - Michael addition - fluorinated alkyne - sodium catalyst - perfluorinated ketals

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