| Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide |
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| 作者姓名： | 汪磊 黄志真 |
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| 作者单位： | Department of Chemistry Zhejiang University，Department of Chemistry Zhejiang University Hangzhou 310027，China，Hangzhou 310027，China |
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| 基金项目： | 中国科学院资助项目，the Postdoctoral Science Foundation of China |
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| 摘 要： | A range of ferrocenyl sulfides are synthesized and screened. Among them 1-α-methysulphoferrocenyl ethyl acetate and 1-α-methysulphoferrocenyl alcohol are found to be unexpected catalysts, which is first reported mediating in sulfur ylide epoxidation reactions, furnishing a novel approach for highly stereoselective synthesis of oxiranes with 98%-100% trans-isomer. The protocol also has excellent yield, convenient workup and recycled starting material. The reason of high trars-selectivity is due to the bulky ferrocenyl sulfide group, which stabilizes the intermediates and determines the trans priority. A possible catalytic mechanism is also proposed.
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| 关 键 词： | 硫化物 接触反应 氧化作用 立体选择性 催化剂 |
| 收稿时间： | 2005-01-31 |
| 修稿时间： | 2005-04-25 |
Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide |
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| Wang Lei,Huang Zhi-zhen.Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide[J].Journal of Zhejiang University Science,2005,6(7):636-639. |
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| Authors: | Wang Lei Huang Zhi-zhen |
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| Institution: | (1) Department of Chemistry, Zhejiang University, 310027 Hangzhou, China |
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| Abstract: | A range of ferrocenyl sulfides are synthesized and screened. Among them 1-α-methysulphoferrocenyl ethyl acetate and 1-α-methysulphoferrocenyl alcohol are found to be unexpected catalysts, which is first reported mediating in sulfur ylide epoxidation reactions, furnishing a novel approach for highly stereoselective synthesis of oxiranes with 98%～100% trans-isomer.The protocol also has excellent yield, convenient workup and recycled starting material. The reason of high trans-selectivity is due to the bulky ferrocenyl sulfide group, which stabilizes the intermediates and determines the trans priority. A possible catalytic mechanism is also proposed. |
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| Keywords: | Ferrocenylsulfide Catalytic ylide epoxidation Stereoselectivity |
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