| Materials & Chemical Engineering |
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| Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide |
| WANG Lei, HUANG Zhi-zhen |
| Department of Chemistry, Zhejiang University, Hangzhou 310027, China |
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Abstract A range of ferrocenyl sulfides are synthesized and screened. Among them 1-a-methysulphoferrocenyl ethyl acetate and 1-a-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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Received: 31 January 2005
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