Facile synthesis of optically active gamma-lactones via lipase-catalyzed reaction of 4-substituted 4-hydroxybutyramides.
Lipase-catalyzed transesterification of racemic 4-substituted 4-hydroxybutyramides with succinic anhydride proceeded enantioselectively to afford (S)-succinic acid monoester and unreacted (R)-4-hydroxybutyramide derivative, which were separated easily by treatment with an alkaline solution. Both enantiomers were converted easily to optically active gamma-substituted gamma-butyrolactones.
Matsumura
Y
Y
Research Center, Toyotama Koryo Co., Ltd., Kanagawa, Japan.
Endo
T
T
Chiba
M
M
Fukawa
H
H
Terao
Y
Y
D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013387:Succinic Anhydrides
D000577:Amides; D007202:Indicators and Reagents; D013387:Succinic Anhydrides; C031801:succinic anhydride; D008049:Lipase; D015107:4-Butyrolactone