245655-48-5Relevant articles and documents
Selective fluorination of (1S,4R)-(-)-camphanic acid with sulphur tetrafluoride: Preparation of new fluorinated optically active derivatives of camphor and 1,2,2-trimethylcyclopentane
Dmowski, Wojciech,Piasecka-Maciejewska, Krystyna
, p. 97 - 100 (2007/10/03)
Treatment of (1S,4R)-(-)-camphanic acid (1) with sulphur tetrafluoride affords (1R,4S)-(-)-3-oxa-4-(trifluoromethyl)camphor (2) as a main product together with small amounts of (1S,4R)-camphanoyl fluoride (3), (1R)-3-(trifluoromethyl)camphonenoyl fluoride (4) and (1R)-3,4-dehydrocamphoroyl difluoride (5). Reduction of 2 with LiAlH4 gives the diol, (1R,3S)-(+)-3-hydroxy-1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanemethanol (6), which when heated with KHSO4 readily dehydrates to (1R,4S)-(-)-3-oxa-4-(trifluoromethyl)bornane (7). Acylation of the diol 6 proceeds regioselectively at the primary hydroxyl group to give exclusively monoacylated derivative 8.