Enantioselective synthesis of hydroxy ketones through cleavage and formation of acyloin linkage. Enzymatic kinetic resolution via C-C bond cleavage

Download
index.pdf
2001-01-01
Demir, Ayhan Sıtkı
Pohl, M
Janzen, E
Muller, M
Show full item record
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
286
views
129
downloads
Both enantiomers of benzoins and (R)-2-hydroxy-1-phenylpropanone analogues were obtained in high yield on a preparative scale starting from aromatic aldehydes, rac-benzoins and aliphatic aldehydes via enzyme-catalysed C-C bond cleavage and C-C bond formation reactions.
Benzoylformate decarboxylase, Dependent enzymes, Organic synthesis, Aldolase, Thiamin, Diphosphate, Benzoin, Acids
https://hdl.handle.net/11511/56453
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Department of Chemistry, Article

Suggestions

Asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohol derivatives and applications in various asymmetric transformation reactions
Odabaş, Serhat; Tanyeli, Cihangir; Department of Chemistry (2007)
The asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohols and their applications in asymmetric borane reduction and enantioselective diethylzinc addition to benzaldehyde reactions were performed starting from meso-anhydride 51 that is the cycloadduct of cyclopentadiene and maleic anhydride. The desymmetrization of meso-anhydride 51 was achieved by using quinine or quinidine with very high enantiomeric excess value (up to 98% ee) and with high chemical yield. The quinine-mediated desymmetrizati...
Enantioselective synthesis of (S)-2-hydroxypropanone derivatives by benzoylformate decarboxylase catalyzed C-C bond formation
Dunnwald, T; Demir, Ayhan Sıtkı; Siegert, P; Pohl, M; Muller, M (2000-06-01)
Chiral 2-hydroxypropanone derivatives 5a-v, 8a-d, and 10a, b were formed by benzoylformate decarboxylase (BFD) catalyzed C-C bond formation. A donor aldehyde and acetaldehyde as an acceptor were carboligated in aqueous buffer solution with remarkable ease in high chemical yield and good to high optical purity. The substrate range of this thiamin diphosphate dependent enzyme was examined to employ this benzoin condensation type reaction in stereoselective synthesis. The observed dependence of the enantiomeri...
Asymmetric synthesis of norbornene based 1,4-Aminoalcohol derivatives and applications in asymmetric diethylzinc reactions
Erdem, Mine; Tanyeli, Cihangir; Department of Chemistry (2007)
The asymmetric synthesis of chiral norbornene based 1,4-aminoalcohols and their applications in asymmetric diethylzinc addition reactions was perfomed starting from meso-anhydride 50. The desymmetrization of this meso-anhydride 50 was done by the usage of quinine or quinidine cinchona alkaloids with very high enantiomeric excess values (up to 98% ee) and chemical yields. The Quinidine-mediated desymmetrization of meso-anhydride 50 with methanol gave (2R,3S)-(+)-cis-monoester 51. The amination of this result...
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%.
Dimethyl ether from syngas and effect of CO2 sorption on product distribution over a new bifunctional catalyst pair containing STA@SBA-15
ÇELİK ÖZCAN, MERVE; PEKMEZCİ KARAMAN, BİRCE; OKTAR, NURAY; Doğu, Timur (2022-12-01)
Direct synthesis of dimethyl ether (DME) from syngas was investigated in the presence of a bifunctional catalyst pair containing silicotungstic acid (STA) incorporated SBA-15 (5, 10, 25% by wt. STA) for the in-situ dehydration of synthesized methanol. The methanol synthesis component of this catalyst mixture is a Cu/ZnO-based commercial (HF) catalytic material. The new STA@SBA-15 type solid acid catalysts synthesized in this study indicated ordered mesoporous structures with surface area values in the range...
Citation Formats
A. S. Demir, M. Pohl, E. Janzen, and M. Muller, “Enantioselective synthesis of hydroxy ketones through cleavage and formation of acyloin linkage. Enzymatic kinetic resolution via C-C bond cleavage,” JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, pp. 633–635, 2001, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56453.
METU IIS - Integrated Information Service open@metu.edu.tr