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Journal of Zhejiang University SCIENCE A 2005 Vol.6 No.7 P.636~639

10.1631/jzus.2005.A0636


Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide


Author(s):  WANG Lei, HUANG Zhi-zhen

Affiliation(s):  Department of Chemistry, Zhejiang University, Hangzhou 310027, China

Corresponding email(s):   leiwangchem@hotmail.com

Key Words:  Ferrocenylsulfide, Catalytic ylide epoxidation, Stereoselectivity


WANG Lei, HUANG Zhi-zhen. Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide[J]. Journal of Zhejiang University Science A, 2005, 6(7): 636~639.

@article{title="Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide",
author="WANG Lei, HUANG Zhi-zhen",
journal="Journal of Zhejiang University Science A",
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%T Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide
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%A HUANG Zhi-zhen
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%P 636~639
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%D 2005
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2005.A0636

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T1 - Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide
A1 - WANG Lei
A1 - HUANG Zhi-zhen
J0 - Journal of Zhejiang University Science A
VL - 6
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EP - 639
%@ 1673-565X
Y1 - 2005
PB - Zhejiang University Press & Springer
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DOI - 10.1631/jzus.2005.A0636


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.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

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[2] Aggarwal, V.K., Charmat, J., Dudin, L., Porcelloni, M., Richardson, J., 2004. Effect of sulfide structure on enantioselectivity in catalytic asymmetric epoxidation of aldehydes: Mechanistic insights and implications. Proc. Nat. Acad. Science (U.S.A.), 101:5467-5471.

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