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

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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

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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.
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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.