Enantioselective synthesis of bridgehead hydroxyl bicyclo[2.2.2]octane derivatives via asymmetric allylindation |
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| Affiliation: | 1. Human Health Therapeutics Portfolio, National Research Council of Canada, 100 Sussex Drive, Ottawa, ON K1A 0R6, Canada;2. Public Health Agency of Canada, Toronto, ON, Canada;1. School of Environment and Chemical Engineering, Nanchang Hangkong University, Nanchang 330063, PR China;2. School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, United States;3. State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, PR China;1. CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China;2. Shanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai, 201210, China;1. Centro de Investigação em Química, Department of Chemistry and Biochemistry, Faculty of Science, University of Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal;2. Instituto de Química Física “Rocasolano”, CSIC, Serrano 119, 28006 Madrid, Spain |
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| Abstract: | A recent new strategy for the transformation of mono-dioxolane protected 1,3-cyclohexadione into bridgehead hydroxyl bicyclo[2.2.2]octane derivatives, based on allylindation followed by ozonolysis and intramolecular aldol addition, was modified to include asymmetric allylindation. This enabled the first enantioselective synthesis of (1R,4R,6S)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2]octan-2-one and (1S,4S,6R)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2]octan-2-one in high enantiomeric excess. Issues concerning the non-reproducibility of the asymmetric allylindation were also addressed. |
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