Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide

• Published in: Journal of Zhejiang University. A. Science Vol. 6; no. 7; pp. 636 - 639
• Main Author: 汪磊 黄志真
• Format: Journal Article
• Language: English
• Published: Department of Chemistry, Zhejiang University, Hangzhou 310027, China 01.07.2005
• Subjects: 催化剂; 接触反应; 氧化作用; 硫化物; 立体选择性; Stereoselectivity; Ferrocenylsulfide; Catalytic ylide epoxidation
• ISSN: 1673-565X; 1862-1775
• DOI: 10.1631/jzus.2005.A0636

A range of ferrocenyl sulfides are synthesized and screened. Among them l-a-methysulphoferrocenyl ethyl acetate and l-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.