Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde.
[reaction: see text] 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.
Demir
Ayhan S
AS
Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey. asdemir@metu.edu.tr
Seşenoglu
Ozge
O
Dünkelmann
Pascal
P
Müller
Michael
M
D000079:Acetaldehyde / Q000737:chemistry*; D000446:Aldehyde-Lyases / Q000737:chemistry* / Q000378:metabolism; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis*; D011551:Pseudomonas fluorescens / Q000201:enzymology; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; D000446:Aldehyde-Lyases; C059416:benzaldehyde lyase; D000079:Acetaldehyde