Lipase-catalyzed chemo- and enantioselective acetylation of 2-alkyl/aryl-3-hydroxypropiophenones.
The chemo- and enantioselective capabilities of porcine pancreatic lipase (PPL) in tetrahydrofuran, and Candida rugosa lipase (CRL) in diisopropyl ether have been investigated for the acetylation of racemic 2-alkyl/aryl-3-hydroxypropiophenones, which are important precursors in the synthesis of biologically active chromanones and isoflavanones. A highly chemoselective acetylation of primary hydroxy group in preference to phenolic hydroxy group leading to the formation of enantiomerically enriched monoacetates has been observed.
Kumar
R
R
Department of Chemistry, University of Delhi, -110 007, Delhi, India.
Azim
A
A
Kumar
V
V
Sharma
S K
SK
Prasad
A K
AK
Howarth
O W
OW
Olsen
C E
CE
Jain
S C
SC
Parmar
V S
VS
D000085:Acetates / Q000737:chemistry; D000107:Acetylation; D000818:Animals; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D002839:Chromans / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D006900:Hydroxylation; D006910:Hydroxypropiophenone / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism*; D007529:Isoflavones / Q000737:chemistry; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D010179:Pancreas / Q000201:enzymology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D013552:Swine
C437563:3-hydroxy-1-(2-hydroxy-3,4-dimethoxyphenyl)-2-methylpropanone; D000085:Acetates; D002839:Chromans; D007529:Isoflavones; D006910:Hydroxypropiophenone; D008049:Lipase