Diastereoselective addition of monoterpenic alcoholates and thiolates to 2,3-dicarbomethoxynorbornadiene |
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| Institution: | 1. Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Campus Universitario, E-28871 Alcalá de Henares, Spain;2. Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Spain;3. Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, Campus Universitario, E-28871 Alcalá de Henares, Spain;1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Ulitsa Vavilova, dom 28, Moscow 119991, Russia;2. Semenov Institute of Chemical Physics, Russian Academy of Sciences, Ulitsa Kosygina, dom 4, Moscow 119991, Russia;1. State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, Hong Kong Baptist University, Hong Kong SAR, China;2. Department of Clinical Oncology, The University of Hong Kong, Hong Kong SAR, China;3. Shenzhen Key Laboratory of Translational Medicine of Tumor and Cancer Research Centre, School of Medicine, Shenzhen University, Shenzhen, China;1. Catalysis and Chemical Reaction Engineering Laboratories, Department of Chemical Engineering, University of Saskatchewan, Saskatoon, SK S7N 5A9, Canada;2. Syncrude Edmonton Research Centre, Edmonton, AB T6N 1H4, Canada;1. School of Pharmacy, China Pharmaceutical University, Nanjing, 211198, China;2. Department of Chemistry, Nanjing University of Information Science & Technology, Nanjing, 210044, China |
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| Abstract: | Addition of excess lithium salts of (−)-menthol or (−)-borneol to 2,3-dicarbomethoxynorbornadiene 1 affords the transesterification–addition products 4 and 5. The thiols derived from the same monoterpenes give only the addition products to the activated double bond, 6 and 7. In all cases, the addition reaction is totally exo-selective with respect to the norbornadiene moiety and moderately selective in discriminating the si- and re-face of the double bond. Both diastereomeric products are formed as a mixture of endo–exo epimers at C3. The major addition product of (−)-menthol to 1 is crystalline, of known absolute configuration, and has potential as a precursor of chiral ligands. |
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