Functionalized dihydropyridines do reduce alkoxycarbene complexes of chromium and give access to polycyclic butenolides |
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| Affiliation: | 1. Ceramic Physics Laboratory, Kyoto Institute of Technology, Sakyo-ku, Matsugasaki, 606-8585 Kyoto, Japan;2. Department of Immunology, Kyoto Prefectural University of Medicine, Kamigyo-ku, Kyoto 602-8566, Japan;3. Department of Dental Medicine, Graduate School of Medical Science, Kyoto Prefectural University of Medicine, Kamigyo-ku, Kyoto 602-8566, Japan;4. Department of Applied Science and Technology, Politecnico di Torino, C.so Duca degli Abruzzi 24, 10129 Turin, Italy;5. SINTX, Technologies, Co. 1885 West 2100 South, Salt Lake City, UT 84119, USA;6. Department of Orthopedic Surgery, Tokyo Medical University, 6-7-1 Nishi-Shinjuku, Shinjuku-ku, 160-0023 Tokyo, Japan;7. The Center for Advanced Medical Engineering and Informatics, Osaka University, Yamadaoka, Suita, 565-0871 Osaka, Japan;1. Peking University-Tsinghua University Center for Life Sciences, Beijing 100871, China;2. Radiochemistry and Radiation Chemistry Key Laboratory of Fundamental Science, Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China;1. Department of Clinical & Experimental Medicine, Section of Internal Medicine, Gerontology & Nutrition, University of Ferrara, Via A. Moro, 8, I-44124 Ferrara, Italy;2. Department of Internal Medicine and Allied Sciences, Atherosclerosis Center, Sapienza University of Rome, Policlinico Umberto I, Viale del Policlinico, 00161 Rome, Italy;3. Department of Biomedical, Metabolic and Neural Sciences, University of Modena & Reggio Emilia, Via Campi 287, I-41125 Modena, Italy;4. Department of Internal Medicine, University of Genova, Viale Bendetto XV, I-16132 Genova, Italy;1. Department of Chemical Physiology and Biochemistry, Oregon Health & Science University, Portland, OR, USA |
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| Abstract: | The dihydropyridine-induced reduction of alkoxycarbene complexes of chromium has been generalized to differently substituted dihydropyridines, e.g. N-benzyl dihydropyridine and N-methyl-N’N’-diethyldihydronicotinamide. In all the cases examined, alkoxyalkynyl carbene complexes lead, upon cascade insertions, to butenolides, the diastereomeric excesses being dependent on the structure of the dihydropyridines. |
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