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

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

272
views

0
downloads

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

Suggestions

OpenMETU
Core

Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds Demir, Ayhan Sıtkı; Akhmedov, IM; Sesenoglu, O (Elsevier BV, 2002-12-02) 2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into beta-enamino, beta-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared in good yield.
Synthesis of various camphor-based chiral pyridine derivatives Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19) (+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.
Synthesis and properties of a novel redox driven chemiluminescent material built on a terthienyl system Atilgan, Nurdan; Algi, Fatih; Önal, Ahmet Muhtar; CİHANER, ATİLLA (Elsevier BV, 2009-07-18) A novel redox driven chemiluminescent material built on a terthienyl system, namely 5,7-di-ethylenedioxythiophen-2-yl-2,3-dihydro-thieno[3,4-d]pyridazine-1,4-dione (ETE-Lum), which is soluble in both organic media and basic aqueous solution was synthesized and characterized. Furthermore, its polymer, PETE-Lum, which is one of the most rare examples of chemiluminescent polymeric materials bearing a pyridazine unit, was obtained successfully by electrochemical means. Both of the materials give chemiluminescen...
Synthesis of the possible carcinogenic dihydrodiol and diol epoxide of phthalazine Ozer, G; Saracoglu, N; Menzek, A; Balcı, Metin (Elsevier BV, 2005-02-07) Inverse-Diels-Alder reaction of dimethyl 1,2,4,5 -tetrazine-3,6-dicarboxylate with benzene cis-diol gave dihydrodiol coninini 2 the 1,4-dihydropyridazine ring. Attempts at oxidation of the dihydropyridazine ring with PIFA and MnO2, resulted in the formation of 5- and 5,6-dihydroxy-phthalazine derivatives. The oxidation of the dihydropyfidazine ring was achieved by way of photooxygenation. The phthalazine type dihydrodiol is unstable and easily undergoes aromatization. The Diels-Alder reaction of tetrazine w...
Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones Zora, Metin; Bueyuekguengoer, Orhan (Elsevier BV, 2007-05-07) The coupling of ferrocenyl alkynes with cyclopropylcarbene-chromium complex leads to ferrocenyl-substituted 2-cyclopentenones with or without a hydroxy substituent, namely 4-cyclopentene-1,3-diones, 2-cyclobutenones, and alpha, beta-unsaturated aldehydes in varying amounts. The reaction initially produces a cyclopentadienone intermediate, then to the double bond of which, bearing a ferrocenyl group, addition of water occurs to afford hydroxy-substituted 2-cyclopentenones. In all the products, the hydroxy gr...

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.