Enantioselective synthesis of 4,5,6,7-tetrahydro-4-oxo-benzofuran-5-yl acetate and 1-benzyl-4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate using chemoenzymatic methods

Date

2007-03-01

Author

Demir, Ayhan Sıtkı
Caliskan, Zerrin
Sahin, Ertan

Metadata

Show full item record

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

Item Usage Stats

146
views

0
downloads

The chemoenzymatic synthesis of both of the enantiomers of pharmacologically interesting compounds such as 4,5,6,7-tetrahydro-4-oxobenzofuran-5-yl acetate (2a), 4,5,6,7-tetrahydro-4-oxo-6,6-dimethylbenzofuran-5-yl acetate (2b), and their hydroxy derivatives 3a, 3b, 1-benzyl4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate (5), starting from 6,7-dihydrobenzofuran-4(5H)-one (la), 6,7-dihydro-6,6-dimethylbenzofuran4(5H)-one (7b), and 1-benzyl-6,7-dihydro-1 H-indol-4(5H)-one (4) are reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated kinetic resolution of alpha'-acetoxy enone provides acetoxy and hydroxy derivatives in good yields and high enantiomeric excesses.

Subject Keywords

Process Chemistry and Technology, Biochemistry, Bioengineering, Catalysis

URI

https://hdl.handle.net/11511/56394

Journal

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC

DOI

https://doi.org/10.1016/j.molcatb.2006.09.006

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Immobilization of dioxomolybdenum(VI) complex bearing salicylidene 2-picoloyl hydrazone on chloropropyl functionalized SBA-15: A highly active, selective and reusable catalyst in olefin epoxidation Bagherzadeh, Mojtaba; Zare, Maryam; Salemnoush, Taghi; Özkar, Saim; Akbayrak, Serdar (Elsevier BV, 2014-04-05) A novel organic-inorganic hybrid heterogeneous catalyst system was obtained from the reaction of the molybdenum(VI) complex of salicylidene 2-picoloyl hydrazone with mesoporous silica containing 3-chloropropyl groups prepared by a direct synthetic approach involving hydrolysis and co-condensation of tetraethylorthosilicate (TEOS) and 3-chloropropyltrimethoxysilane in the presence of the triblock copolymer P123 as template under acidic conditions. Characterization of the functionalized materials by X-ray dif...
Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl)ethan-1-ol as a flexible building block for the preparation of serine and azasugars Demir, Ayhan Sıtkı; Sesenoglu, O; Aksoy-Cam, H; Kaya, H; Aydogan, K (Elsevier BV, 2003-05-16) The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)- and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl)ethan-1-ol with an ee of up to 96%.
L-Dopa synthesis using tyrosinase immobilized on magnetic beads Tuncagil, Sevinc; Kayahan, Senem; BAYRAMOĞLU, GÜLAY; ARICA, MEHMET YAKUP; Toppare, Levent Kamil (Elsevier BV, 2009-06-01) Magnetic beads were prepared via Suspension polymerization of glycidyl methacrylate (GMA) and methyl methacrylate (MMA) in the presence of ferric ions. Following polymerization, thermal co-precipitation of the Fe(III) ions in the beads with Fe(II) ions under alkaline condition resulted in encapsulation of Fe3O4 nano-crystals within the polymer matrix. The magnetic beads were activated with glutaraldehyde, and tyrosinase enzyme was covalently immobilized on the support via reaction of amino groups under mild...
Palladium doped perovskite-based NO oxidation catalysts: The role of Pd and B-sites for NOx adsorption behavior via in-situ spectroscopy Say, Zafer; Dogac, Merve; Vovk, Evgeny I.; Kalay, Yunus Eren; KIM, Chang Hwan; LI, Wei; Ozensoy, Emrah (Elsevier BV, 2014-07-01) Perovskite-based materials (LaMnO3, Pd/LaMnO3, LaCoO3 and Pd/LaCoO3) were synthesized, characterized (via BET, XRD, Raman spectroscopy, XPS and TEM) and their NO (x= 1,2) adsorption characteristics were investigated (via in-situ FTIR and TPD) as a function of the nature of the B-site cation (i.e. Mn vs Co), Pd/PdO incorporation and H-2-pretreatment. NO adsorption on of LaMnO3 was found to be significantly higher than LaCoO3, in line with the higher SSA of LaMnO3. Incorporation of PdO nanoparticles with an a...
Synergistic Effects in Bimetallic Palladium-Copper Catalysts Improve Selectivity in Oxygenate Coupling Reactions Goulas, Konstantinos A.; SREEKUMAR, Sanil; Song, Yuying; Kharidehal, Purnima; Günbaş, Emrullah Görkem; Dietrich, Paul J.; Johnson, Gregory R.; Wang, Y. C.; Grippo, Adam M.; Grabow, Lars C.; Gokhale, Amit A.; Toste, F. Dean (American Chemical Society (ACS), 2016-06-01) Condensation reactions such as Guerbet and aldol are important since they allow for C-C bond formation and give higher molecular weight oxygenates. An initial study identified Pd-supported on hydrotalcite as an active catalyst for the, transformation, although this catalyst showed extensive undesirable decarbonylation. A catalyst containing Pd and Cu in a 3:1 ratio dramatically decreased decarbonylation, while preserving the high catalytic rates seen with Pd-based catalysts. A combination of XRD, EXAFS, TEM...

Citation Formats

A. S. Demir, Z. Caliskan, and E. Sahin, “Enantioselective synthesis of 4,5,6,7-tetrahydro-4-oxo-benzofuran-5-yl acetate and 1-benzyl-4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate using chemoenzymatic methods,” JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, pp. 87–92, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56394.