Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones.
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.
Lu
Xiaojie
X
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Liu
Yan
Y
Sun
Bingfeng
B
Cindric
Brittany
B
Deng
Li
L
D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D010084:Oxidation-Reduction; D010545:Peroxides / Q000138:chemical synthesis; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D007659:Ketones; D010545:Peroxides; D006861:Hydrogen Peroxide