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Title
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Application of pyridyl Trost ligand in asymmetric allylic oxidation
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Type
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Presentation
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Keywords
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Kharasch–Sosnovsky reaction,enantiomeric excess,allylic oxidation, Trost ligand
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Abstract
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Asymmetric allylic oxidation of olefins with peresters in the presence of copper salts (known as the Kharasch–Sosnovsky reaction) is a significant transformation in asymmetric organic synthesis. Through this reaction, a new functional group (carboxyl) is formed and the olefinic double bond isn’t changed [1]. In the course of our studying on asymmetric synthesis, at first the optically active pyridyl Trost ligand was easily prepared from available starting material [2] and then, we utilized this ligand in asymmetric allylic oxidation of cyclic olefins under various conditions. The best yields (93%) and reasonable enantiomeric excess (35%) was obtained in low temperature (-10 °C) and in the solvent of acetonitile and in the presence of catalytic amount of copper (I) hexafluorophosphate (10%). Also it was further to note that adding a few drops more of phenylhydrazine reduced reaction time and increased ee% of desirable allylic esters.
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Researchers
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Khosrow Jadidi (Fourth Researcher), Farbod Salahi (Third Researcher), Saadi Samadi (Second Researcher), Hamid Arvinnezhad (First Researcher)
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