Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
Asymmetric Synthesis of Optically Active Lactones from Cyclic Acid Anhydrides Using Lipase in Organic Solvents1)
Yukio YAMAMOTOKazuyoshi YAMAMOTOTakaaki NISHIOKAJun'ichi ODA
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Volume 52 (1988) Issue 12 Pages 3087-3092

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Abstract

Under heterogeneous conditions, a lipase (Amano P) catalyzed the asymmetric ring opening of 3-substituted glutaric anhydrides with 1-butanol in diisopropyl ether to afford the R mono esters, which were converted to the 3-substituted δ-lactones having 60-93%e.e. This process offered a practical means for preparing optically active 3-methyl-δ-valerolactone (93%e.e.) which is a useful chiral building block. The enzyme hydrolyzed the corresponding dimethyl esters to give the S mono esters in an aqueous medium. In both reactions, the pro R carbonyl group was preferentially attacked to yield pairs of enantiomers.

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