Chiral synthons from α-pinene: enantioselective syntheses of bicyclo[3.3.0] and [3.2.1]octanones |
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| Institution: | 1. Department of Chemistry, Georgia Southern University, 521 College of Education Drive, Statesboro, GA 30460-8064, USA;2. Department of Biology, Georgia Southern University, 1332 Southern Drive, Statesboro, GA 30460-8042, USA;1. Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto Daigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan;2. JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan;1. Department of Computer Science and Information Engineering, Chang Gung University, Taoyuan 33302, Taiwan;2. Department of Computer Science, National Tsing Hua University, Hsinchu 30013, Taiwan;3. Biomedical Technology and Device Research Laboratories, Industrial Technology Research Institute, Hsinchu 30011, Taiwan;4. Department of Computer Science and Information Engineering, Providence University, Taichung 43301, Taiwan;1. Saint-Petersburg State University, University emb. 7/9, St. Petersburg, 199034, Russian Federation;2. Saint-Petersburg Academic University – Nanotechnology Research and Education Centre RAS, Khlopin str. 8/3, St-Petersburg, 194021, Russian Federation;3. Pavlov First Saint Petersburg State Medical University, L''va Tolstogo str. 6/8, St. Petersburg, 197022, Russian Federation;4. Voeikov Main Geophysical Observatory, ul. Karbysheva 7, St. Petersburg, 194021, Russian Federation |
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| Abstract: | Enantioselective syntheses of bicyclo3.3.0]octan-3-one, bicyclo3.2.1]octan-3-one and bicyclo3.2.1]octan-2-one derivatives were accomplished by employing a chiron based approach, using intramolecular rhodium carbenoid C–H insertion, acid catalysed cyclisation of α-diazo ketone and intramolecular type II carbonyl ene reactions as key steps. |
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