Polymer-supported ruthenium porphyrins: Versatile and robust epoxidation catalysts with unusual selectivity

被引:144
作者
Yu, XQ
Huang, JS
Yu, WY
Che, CM
机构
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
[2] Univ Hong Kong, HKU, CAS Joint Lab New Mat, Hong Kong, Hong Kong, Peoples R China
关键词
D O I
10.1021/ja000461k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbonyl ruthenium(II) 5,10,15-tris(4-R-phenyl)-20-(4-hydroxyphenyl)porphyrins (R = Cl, Me) covalently attached Co Merrifield's peptide resin were prepared. The catalyst with R = Cl was found to efficiently catalyze Cl(2)pyNO epoxidation of a wide variety of alkenes, including aromatic and aliphatic terminal alkenes, cis- and trans-stilbene, cyclohexene and cyclooctene, alpha,beta-unsaturated ketones, conjugated enyne, glycal, and protected alpha-amino alkene. Unusual selectivities were observed for the epoxidations of 1,5-cyclooctadiene,cis-1-phenyl-3-penten-1-yne (9), 3,4,6-tri-O-acetyl-D-glucal (11), and 2-(Boc-amino)-1-phenylbut-3-ene (13), which feature a complete bisepoxide selectivity (1,5-cyclooctadiene), unprecedentedly high cis:trans ratio (9), and complete diastereoselectivity (11 and 13). The new heterogenized metalloporphyrin epoxidation catalysts are of high stability and reusability.
引用
收藏
页码:5337 / 5342
页数:6
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