A novel modification of the Ritter reaction: stereoselective synthesis of bridgehead-fused Δ2-norbornanethiazolines from thiocamphor and thiofenchone |
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| Institution: | 1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, UCM, Ciudad Universitaria, 28040 Madrid, Spain;2. Instituto Universitario de Investigación, Facultad de Ciencias, UNED, Ciudad Universitaria, 28040 Madrid, Spain;1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, China;2. Department of Theoretical Chemistry and Biology, School of Biotechnology, KTH Royal Institute of Technology, Stockholm 10691, Sweden;1. Department of Organic Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary;2. Department of Biochemistry, University of Szeged, Dóm tér 9., H-6720 Szeged, Hungary;3. Cereal Research Non-Profit Ltd., P.O. Box 391, H-6701 Szeged, Hungary;4. Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary;1. Key Laboratory on Luminescence and Real-Time Analysis, Ministry of Education, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, PR China;2. School of Chemistry and Environmental Engineering, Chongqing Three Gorges University, Chongqing, Wanzhou 404000, China;1. College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 34134, Republic of Korea;2. College of Pharmacy, Chungbuk National University, Cheongju 19421, Republic of Korea |
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| Abstract: | An easy two-step route for the stereoselective synthesis of novel bridgehead-fused norbornanethiazolines from readily available natural camphor and fenchone is described. The key step of the synthetic route is the highly stereoselective trapping of 1-(trifluoromethylsulfonylthio)-2-norbornyl cations by nitriles followed by intramolecular cyclization, which constitutes a new modification of the Ritter reaction. |
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