Synthesis of α-(Pentafluorosulfanyl)- and α-(Trifluoromethyl)-Substituted Carboxylic Acid Derivatives by Ireland–Claisen Rearrangement
| Autor: | Christian Mück-Lichtenfeld, Andrej V. Matsnev, Günter Haufe, Joseph S. Thrasher, Bernd Beutel, Anna-Lena Dreier |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Trifluoromethyl Trimethylsilyl 010405 organic chemistry Stereochemistry Carboxylic acid Organic Chemistry Substituent Diastereomer 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Triethylamine Trifluoromethanesulfonate Ireland–Claisen rearrangement |
| Zdroj: | The Journal of Organic Chemistry. 82:1638-1648 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.6b02805 |
| Popis: | Earlier studies have shown that [3,3]-sigmatropic rearrangements of allyl esters are useful for the construction of fluorine-containing carboxylic acid derivatives. This paper describes the synthesis of 3-aryl-pent-4-enoic acid derivatives bearing either a pentafluorosulfanyl (SF5) or a trifluoromethyl (CF3) substituent in the 2-position by treatment of corresponding SF5- or CF3-acetates of p-substituted cinnamyl alcohols with triethylamine followed by trimethylsilyl triflate (TMSOTf). This Ireland–Claisen rearrangement delivered approximate 1:1 mixtures of syn/anti diastereoisomers due to tiny differences ( |
| Databáze: | OpenAIRE |
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