Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones |
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Authors: | Lu Xiaojie Liu Yan Sun Bingfeng Cindric Brittany Deng Li |
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Affiliation: | Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA. |
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Abstract: | Despite the potential of chiral peroxides as biologically interesting or even clinically important compounds, no catalytic enantioselective peroxidation has been reported. With a chiral catalyst not only to induce enantioselectivity but also to convert a well established epoxidation pathway into a peroxidation pathway, the first efficient catalytic peroxidation has been successfully developed. Employing readily available alpha,beta-unsaturated ketones and hydroperoxides and an easily accessible cinchona alkaloid catalyst, this novel reaction will open new possibilities in the asymmetric synthesis of chiral peroxides. Under different conditions a highly enantioselective epoxidation with the same starting materials, reagents, and catalyst has was also established. |
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