Benzaldehyde lyase catalyzed enantioselective self and cross condensation reactions of acetaldehyde derivatives

Date

2011-01-01

Author

Ayhan, Peruze
Turan, Ilke Simsek
Cifci, Burce
Demir, Ayhan Sıtkı

Metadata

Show full item record

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

Item Usage Stats

138
views

0
downloads

Flexible protected 1,3,4-trihydroxy-2-butanone is synthesized in high enantiomeric excesses by using asymmetric homo- and cross- acyloin coupling of aliphatic aldehydes catalyzed by benzaldehyde lyase.

Subject Keywords

Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry

URI

https://hdl.handle.net/11511/62912

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY

DOI

https://doi.org/10.1039/c0ob01121e

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde Demir, Ayhan Sıtkı; Sesenoglu, O; Dunkelmann, P; Muller, M (American Chemical Society (ACS), 2003-06-12) Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to carboligation.
Carboligation reactions with benzaldehyde lyase immobilized on superparamagnetic solid support Sopaci, S. Betuel; Turan, Ilke Simsek; Tural, Bilsen; Volkan, Mürvet; Demir, Ayhan Sıtkı (Royal Society of Chemistry (RSC), 2009-01-01) Histidine-tagged recombinant benzaldehyde lyase (BAL, EC 4.1.2.38) was efficiently immobilized to surface-modified magnetic particles with affinity ligand binding. In addition to conventional benzoin condensation reactions, two important representative BAL-catalyzed carboligation reactions, were also performed with this magnetically responsive biocatalyst. The results obtained from the carboligation reactions that were performed with this simple and convenient heterogenous biocatalyst were comparable to tha...
Organosilanols as Catalysts in Asymmetric Aryl Transfer Reactions Özçubukçu, Salih; BOLM, Carsten (American Chemical Society (ACS), 2005-03-01) Various ferrocene-based organosilanols have been synthesized in four steps starting from achiral ferrocene carboxylic acid. Applying these novel planar-chiral ferrocenes as catalysts in asymmetric phenyl transfer reactions to substituted benzaldehydes afforded products with high enantiomeric excesses. The best result (91% ee) was achieved in the addition to p-chlorobenzaldehyde with organosilanol 2b, which has a tert-butyl substituent on the oxazoline ring and an isopropyl group on the silanol fragment.
Synthesis of ferrocenyl quinolines Zora, Metin (Elsevier BV, 2008-06-01) A convenient one-pot synthesis of ferrocenyl-substituted quinolines via a molecular iodine-catalyzed reaction of ferrocenylimines with enolizable aldehydes is reported. First, nucleophilic addition of the in situ generated enol to ferrocenylimine produces beta-anilinopropionaldehyde, which then undergoes intramolecular Friedel-Crafts reaction to give dihydroquinoline derivative. Finally, subsequent dehydration and aerobic oxidation affords ferrocenyl quinolines.
Coupling of ferrocenyl chromium carbene complex with cyclobutenediones Zora, Metin; Bekir Peynircioglu, N. (Elsevier BV, 2002-08-15) The coupling of ferrocenyl chromium carbene complex with cyclobutenediones leads to ferrocenyl-substituted 5-alkylidenefuranones and 4-cyclopentene-1,3-diones, methyl ferrocenoate and acetylferrocene in varying amounts. The scope and limitations of these processes are investigated. In comparison with the phenyl analog, ferrocenyl chromium carbene complex has been found to be less reactive. This is also supported by PM3 calculations. The coupling of ferrocenyl chromium carbene complex with cyclobutenediones...

Citation Formats

P. Ayhan, I. S. Turan, B. Cifci, and A. S. Demir, “Benzaldehyde lyase catalyzed enantioselective self and cross condensation reactions of acetaldehyde derivatives,” ORGANIC & BIOMOLECULAR CHEMISTRY, pp. 2602–2605, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62912.