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Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones.

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.

SUBMITTER: Lu X

PROVIDER: S-EPMC2652727 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones.

Lu Xiaojie X Liu Yan Y Sun Bingfeng B Cindric Brittany B Deng Li L

Journal of the American Chemical Society 20080605 26

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 ...[more]

PMID: 18529055

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