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Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines
Journal article   Peer reviewed

Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines

Franklin A. Davis, Hu Liu, Bang-Chi Chen and Ping Zhou
Tetrahedron, v 54(35), pp 10481-10492
1998

Abstract

The oxidation of 1,3-dicarbonyl compounds with (camphorylsulfonyl)oxaziridines 2 was studied in both cyclic and acyclic systems. Two reaction pathways were identified: enolate α-hydroxylation and a novel Baeyer-Villiger type oxidation. The Baeyer-Villiger oxidation product was observed only for the ketones and arises via rearrangement of an alkoxy epoxide. Synthetically useful ee's (82–95%) were observed only for enolates of β-ketoesters where the keto group is part of a 6-membered ring. The oxidation of 1,3-dicarbonyl compounds with (camphorylsulfonyl)oxaziridines 2 was studied in both cyclic and acyclic systems. Two reaction pathways were identified: enolate α-hydroxylation and a novel Baeyer-Villiger type oxidation.

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Collaboration types
Domestic collaboration
Web of Science research areas
Chemistry, Organic
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