Synthesis of substituted tetrahydropyridines by cyclizations of silicon-containing iminium ions |
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| Affiliation: | 1. School of Materials Science and Engineering, Harbin Institute of Technology (Weihai), Weihai 264209, PR China;2. School of Materials Science and Engineering, Harbin Institute of Technology, Harbin 150001, PR China;1. Department of Chemistry and Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, USA;2. Department of Biology, Georgia State University, Atlanta, GA 30303, USA;3. Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA;4. Department of Hematology, Kumamoto University of Medicine, Kumamoto 860-8556, Japan;5. Department of Infectious Diseases, Kumamoto University of Medicine, Kumamoto 860-8556, Japan;6. Experimental Retrovirology Section, HIV and AIDS Malignancy Branch National Cancer Institute, Bethesda, MD 20892, USA;7. Department of Refractory Viral Infection, National Center for Global Health and Medicine Research Institute, Shinjuku, Tokyo 162-8655, Japan |
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| Abstract: | Trans-2,6-disubstituted-1,2,5,6-tetrahydropyridines are formed stereoselectively from the cyclization of silicon-containing iminium cations 5 if the nitrogen substituent R1 is an alkyl group. In contrast, cyclization of the corresponding NH or N-acyl iminium ions occurs in a stereorandom fashion. Nonracemic tetrahydropyridines cannot be prepared in this way, since both iminium ion and N-acyliminium ion intermediates racemize prior to cyclization. |
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