Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium

被引：9
|
作者：
Amato, Maria E. [1 ]
Ballistreri, Francesco P. [1 ]
Pappalardo, Andrea [1 ]
Tomaselli, Gaetano A. [1 ]
Toscano, Rosa M. [1 ]
Sfrazzetto, Giuseppe Trusso [1 ]
机构：
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
来源：
MOLECULES | 2013年 / 18卷 / 11期
关键词：
natural compounds oxidation; hydrogen peroxide; methyltrioxorhenium; MAIN-GROUP ELEMENTS; DIASTEREOSELECTIVE CATALYTIC EPOXIDATION; HYDROLYTIC KINETIC RESOLUTION; METHYLRHENIUM TRIOXIDE; TERMINAL EPOXIDES; TRANSITION-METALS; MULTIPLE BONDS; MONOEPOXY OCTADECADIENOATES; SPECTRAL CHARACTERIZATION; GRAPEFRUIT JUICE;
D O I：
10.3390/molecules181113754
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), alpha-ionone (3), beta-ionone (4), methyl linolelaidate (5), methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/H2O2/pyridine. The reactions, performed in CH2Cl2/H2O at 25 degrees C, have shown good regio- and stereoselectivity. The oxidation products were isolated by HPLC or silica gel chromatography and characterized by MS(EI), H-1-, C-13-NMR, APT, gCOSY, HSQC, TOCSY and NOESY measurements. The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects.
引用
收藏
页码：13754 / 13768
页数：15
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