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 inOrganic letters Vol. 5; no. 12; pp. 2047 - 2050
Main Authors Demir, Ayhan S, Şeşenoglu, Özge, Dünkelmann, Pascal, Müller, Michael
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.06.2003
Amer Chemical Soc
Subjects
Acetaldehyde - chemistry
Aldehyde-Lyases - chemistry
Aldehyde-Lyases - metabolism
Aldehydes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Ketones - chemical synthesis
Physical Sciences
Pseudomonas fluorescens - enzymology
Science & Technology
Stereoisomerism
HYDROXY KETONES
CYTOKINE MODULATOR
DEPENDENT ENZYMES
LIGNANS
CYTOXAZONE
NEOLIGNANS
STEREOSELECTIVE SYNTHESIS
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol034415b