Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones

Date

1998-05-22

Author

Demir, Ayhan Sıtkı
Hamamcı, Haluk
Tanyeli, Cihangir
Akhmedov, Idris M.
DOGANEL, Fatos

Metadata

Show full item record

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

Item Usage Stats

176
views

0
downloads

Mn(OAc)(3) oxidation of aromatic ketones afforded the alpha-acetoxy ketones in good yield. Selective hydrolysis of the acetoxy ketones by the fungus Rhizopus oryzae yields (R)-hydroxy ketones in high enantiomeric excess.

Subject Keywords

Manganese(iii) acetate, Asymmetric oxidation, Carboxylic-acids, Bakers-yeast, Stereochemistry, Hydroxylation, Combination, Resolution, Chemistry, Alcohols

URI

https://hdl.handle.net/11511/32186

Journal

Tetrahedron Asymmetry

DOI

https://doi.org/10.1016/s0957-4166(98)00165-7

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01) 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 ph...
OXIDATION OF ARYL ALKYL KETONES TO ALPHA-ACYLOXY, ALPHA-(CAMPHORSULFONYLOXY), OR ALPHA-HYDROXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS OR (1S)-(+)-10-CAMPHORSULFONIC ACID DEMIR, AS; CAMKERTEN, N; AKGUN, H; Tanyeli, Cihangir; MAHASNEH, AS; WATT, DS (Informa UK Limited, 1990-01-01) The α-oxidation of aryl alkyl ketones using manganese(III) acetate in the presence of various carboxylic acids and (1S)-(+)-10-camphorsulfonic acid provided a convenient synthesis of α-acyloxy, α-(10-camphorsulfonyloxy), and α-hydroxy derivatives in good yield.
Synthesis and photooxygenation of homochiral 2-methylpyrrole derivatives of chiral amino alcohols: simple, selective access to chiral bicyclic lactams Aydogan, F; Demir, Ayhan Sıtkı (2004-01-26) Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amino alcohols and 5-chloro-3-pentene-2-one. The photooxygenation of these compounds in the presence of a photosynthesizer furnishes the pyrrolooxazolone structures in high diastereoselectivities. In all of the examples, trans-isomers are formed as the major products.
Synthesis of a novel poly(arylene ether ketone) and its conducting composites with polypyrrole Selampinar, F; Akbulut, Ural; Yildiz, E; Gungor, A; Toppare, Levent Kamil (1997-08-01) The synthesis of a 1,3-bis(4-fluorobenzoyl)-5-tert-butyl benzene and hexafluoro bisphenol A based poly(arylene ether ketone) (PEK) was described. The electrically conductive composites of polypyrrole (PPy) and PEK were formed by electropolymerization of pyrrole on a PEK coated platinum electrode in a medium containing water and p-toluenesulfonic acid as the solvent and the electrolyte, respectively. The electrical conductivity of the composites was found to be between 1 and 4 S/cm. The polypyrrole/poly( eth...
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005) A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...

Citation Formats

A. S. Demir, H. Hamamcı, C. Tanyeli, I. M. Akhmedov, and F. DOGANEL, “Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones,” Tetrahedron Asymmetry, pp. 1673–1677, 1998, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/32186.