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Synlett 1992; 1992(2): 146-148
DOI: 10.1055/s-1992-21296
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First Direct Access to Angularly Trifluoromethyl-Substituted Tricyclic Compounds via a Diels-Alder Reaction Performed with a Trialkyl Olefin

Jean-Pierre Bégué* , Danièle Bonnet-Delpon, Thierry Lequeux, Jean d'Angelo, André Guingant
  • *CNRS-CERCOA, 2 rue Henry Dunant, F-94320 Thiais, France
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Publication Date:
08 March 2002 (online)

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Diels-Alder reactions performed with Danishefsky's diene (1-methoxy-3-trimethylsiloxy-1,3-butadiene) and α-trifluoromethylstyrene (1) or 1-trifluoromethyl-3,4-dihydronaphthalene (2) under high pressure provide tertiary trifluoromethylated alicyclic compounds. An angularly trifluoromethylated A/B cis-phenanthrone, (4aR,10aR)-4a-trifluoromethyl-4a,9, 10,10a-tetrahydrophenanthren-2(1H)-one (6), is obtained by a very short route from ethyl trifluoroacetate.