The synthesis of chiral β-ketosulfoxides by enantioselective oxidation and their stereocontrolled reduction to β-hydroxysulfoxides |
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| Affiliation: | 1. Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan;2. Kyushu Research Center, Forestry & Forest Products Research Institute, 4-11-16 Kurokami, Kumamoto, Kumamoto 860-0862, Japan;3. Japan Synchrotron Radiation Research Institute, SPring-8, 1-1-1 Kouto, Sayo-cho, Sayo-gun, Hyogo 679-5198, Japan;4. Instrumentation Analysis Center, Tokyo University of Agriculture and Technology Koganei, Tokyo 184-8588, Japan;5. Research Institute of Green Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan;6. Graduate School of Agriculture, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan;1. MOE Key Laboratory of Cluster Science, School of Chemistry, Beijing Institute of Technology, Beijing 100081, China;2. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China |
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| Abstract: | Various chiral non-racemic β-ketosulfoxides, a class of compounds frequently used in asymmetric synthesis, were prepared in good yields by tert-butyl hydroperoxide oxidation of the corresponding sulfides in the presence of a complex between titanium and (S,S)-hydrobenzoin. The ee values of almost all of the purified products were >98%. As ascertained by X-ray analysis and/or by NMR spectroscopy, the use of the (S,S)-form of the ligand led to aryl β-ketosulfoxides with (RS)-configuration and to methyl phenacyl sulfoxide with the (SS)-configuration. Some of the aryl ketosulfoxides were subjected to reduction with DIBAL-H/ZnCl2 and the corresponding β-sulfinylalcohols with an (R,RS)-configuration produced. |
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