A Diels–Alder approach to the enantioselective construction of fluoromethylated stereogenic carbon centers
2011
Shibatomi, Kazutaka | Kobayashi, Fumito | Narayama, Akira | Fujisawa, Ikuhide | Iwasa, Seiji
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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