Summary.
A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps – nucleophilic displacement reaction, Claisen, and finally Cope rearrangement – which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to α-trifluoromethyl-γ-ketoacids.
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Burger, K., Hennig, L., Fuchs, A. et al. Domino Reactions with Fluorinated Five-membered Heterocycles – Syntheses of Trifluoromethyl Substituted Butenolides and γ-Ketoacids. Monatsh. Chem. 136, 1763–1779 (2005). https://doi.org/10.1007/s00706-005-0366-z
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DOI: https://doi.org/10.1007/s00706-005-0366-z