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

页码：13754 / 13768

页数：15

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