A Diels-Alder approach to the enantioselective construction of fluoromethylated stereogenic carbon centers |
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| Authors: | Shibatomi Kazutaka Kobayashi Fumito Narayama Akira Fujisawa Ikuhide Iwasa Seiji |
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| Affiliation: | Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Toyohashi 441-8580, Japan. shiba@ens.tut.ac.jp |
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| Abstract: | Highly enantioselective Diels-Alder reactions of β-fluoromethylacrylates were carried out in the presence of a Lewis acid activated chiral oxazaborolidine catalyst. These reactions yielded fluoromethylated cyclohexenes, including trifluoromethyl-, difluoromethyl-, and monofluoromethyl cyclohexenes, as nearly pure enantiomers. The resulting fluoromethyl cyclohexenes were converted into potential synthetic intermediates for bioactive compounds. |
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