A valuable synthetic route to spiro-cyclopropane derivatives containing multiple stereogenic centers |
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| Affiliation: | 1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran;2. Persian Gulf Marine Biotechnology Research Center, The Persian Gulf Biomedical Research Center, Bushehr University of Medical Sciences, Bushehr, Iran;1. MOE Key Laboratory of Thermo-Fluid Science and Engineering, School of Energy and Power Engineering, Xi''an Jiaotong University, Xi''an 710049, PR China;2. School of Engineering, The University of Edinburgh, Edinburgh EH9 3FB, UK;3. State Key Laboratory for Strength and Vibration of Mechanical Structures, Shaanxi Key Laboratory of Environment and Control for Flight Vehicle, School of Aerospace, Xi''an Jiaotong University, Xi''an 710049, China;1. Tetra Pak Processing Systems, Lund, Sweden;2. Lund University, Food Technology, Engineering and Nutrition, Lund, Sweden;3. Kristianstad University, Food and Meal Science, Kristianstad, Sweden;1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran;2. The Persian Gulf Marine Biotechnology Research Center, The Persian Gulf Biomedical Sciences Research Institute, Bushehr University of Medical Sciences, Bushehr, Iran |
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| Abstract: | The unusual, functionalized spiro-cyclopropane derivatives containing four stereogenic centers 8a–8f were obtained in good yields with d.e. ≥98% via tandem double Michael addition/internal nucleophilic substitution of the novel chiral synthon, 5-l-menthyloxy-3-bromo-2(5H)-furanone 5a, with various oxygen nucleophiles under mild conditions. (S)-(−)-Ethyl lactate also reacted under the same conditions to afford the corresponding spiro-cyclopropane derivative 8g. Interestingly, reaction of 5a with ethyl bromo- and chloroacetate, in the usual manner, gave the spiro-cyclopropane 8h rather than the expected C-linked derivative. The absolute configuration of the interesting spiro-cyclopropanes 8 was established by X-ray crystallography. These results provide a valuable synthetic route to some complex molecules containing the spiro-cyclopropane skeleton with multiple stereogenic centers. |
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