Tetrahedron p. 10481 - 10492 (1998)
Update date:2022-07-29
Topics:
Davis, Franklin A.
Liu, Hu
Chen, Bang-Chi
Zhou, Ping
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.
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