Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes |
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| Institution: | 1. Departamento de Qu??mica Orgánica, Facultad de Ciencias, Universidad de Extremadura, 06071 Badajoz, Spain;2. Department of Chemistry, University of Southampton, Southampton SO17 1BJ, UK;1. Drug Resistance Mechanisms and Membrane Proteins Laboratory, BMSSI UMR 5086 CNRS/Université Lyon 1, Institut de Biologie et Chimie des Protéines, Lyon, France;2. Toxicology Department, Faculty of Pharmacy, Univ. Medicine and Pharmacy ¨Iuliu Hatieganu¨, Cluj-Napoca, Romania;3. Univ. Grenoble Alpes, Département de Pharmacochimie Moléculaire DPM UMR 5063, 38041 Grenoble, France;4. CNRS, DPM UMR 5063, 38041 Grenoble, France;5. Université de Lyon, Université Lyon 1, Faculté de Pharmacie – ISPB, EA 4446 Bioactive Molecules and Medicinal Chemistry, SFR Santé Lyon-Est CNRS UMS3453 – INSERM US7, 8 Avenue Rockefeller, F-69373 Lyon Cedex 8, France;6. Department of Applied Biology and Chemical Technology, and State Key Laboratory of Chirosciences, The Hong Kong Polytechnic University, Hung Hom, Hong Kong Special Administrative Region;1. School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, Changzhou University, Changzhou 213164, PR China;2. College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325000, PR China;1. Department of Applied Chemistry, Anhui Agricultural University, Hefei 230036, China;2. Department of Chemistry, University of Science and Technology of China, Hefei 230026, China |
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| Abstract: | The denitrohydrogenation of chiral 4-alkyl-5-glyco-4-nitrocyclohex-1-enes (1 and 3) with tri-n-butyltin hydride and azobisisobutironitrile proceeded in a completely stereoselective way. In each case, the hydrogen atom provided by tri-n-butyltin hydride adds to a free radical intermediate in a trans mode to the adjacent, sterically demanding, sugar side-chain. Attempts to perform denitroalkylation reactions of 1a, 3a or 8 with electron-deficient alkenes yielded only denitrohydrogenated products. |
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