Benzaldehyde Lyase-Catalyzed Enantioselective Carboligation of Aromatic Aldehydes with Mono- and Dimethoxy Acetaldehyde

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 link...

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Bibliographic Details
Published in:Organic letters 2003-06, Vol.5 (12), p.2047-2050
Main Authors: Demir, Ayhan S, Şeşenoglu, Özge, Dünkelmann, Pascal, Müller, Michael
Format: Article
Language:English
Subjects:
Acetaldehyde - chemistry
Aldehyde-Lyases - chemistry
Aldehyde-Lyases - metabolism
Aldehydes - chemistry
Catalysis
Ketones - chemical synthesis
Pseudomonas fluorescens - enzymology
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol034415b