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Synlett 1998; 1998(8): 927-929
DOI: 10.1055/s-1998-1817
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Fluorine-Directed Nazarov Cyclizations 2: Regioselective Synthesis of 5-Trifluoromethyl-2-cyclopentenones

Junji Ichikawa* , Masaki Fujiwara, Tatsuo Okauchi, Toru Minami
  • *Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804-8550, Japan; Fax 81 93 884 3314; E-mail: ichikawa@che.kyutech.ac.jp
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Publication Date:
31 December 2000 (online)

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1-Trifluoromethylvinyl vinyl ketones are treated with trimethylsilyl trifluoromethanesulfonate in CH2Cl2-1,1,1,3,3,3-hexafluoro-2-propanol to afford 5-trifluoromethyl-2-cyclopentenones. Both acyclic and cyclic substrates furnish the corresponding cyclized products in good to excellent yields with defined placement of the endocyclic double bond due to the strong electronic effect exerted by the trifluoromethyl group.

fluorinated divinylketone - Nazarov cyclization - Lewis acid - carbocation - trifluoromethylated cyclopentenone