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.

DOI: 10.1021/ja802982h

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@article{Lu2008CatalyticEP, title={Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones.}, author={Xiaojie Lu and Yan Liu and Bingfeng Sun and Brittany Cindric and Li Deng}, journal={Journal of the American Chemical Society}, year={2008}, volume={130 26}, pages={8134-5} }