Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones

Date

2008-12-01

Author

Demir, Ayhan Sıtkı
Aybey, Asuman

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The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords phenolic alpha-hydroxycarboxylic acid derivatives.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/62598

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2008.09.035

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir and A. Aybey, “Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones,” TETRAHEDRON, pp. 11256–11261, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62598.