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Synthesis 2015; 47(17): 2635-2640
DOI: 10.1055/s-0034-1380753
DOI: 10.1055/s-0034-1380753
paper
Regioselective Synthesis of α-Perfluoroalkylated Ketals via Double Michael Addition of Alcohols to Activated Alkynes
Further Information
Publication History
Received: 11 February 2015
Accepted after revision: 16 April 2015
Publication Date:
17 June 2015 (online)
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 ketalsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380753.
- Supporting Information
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