Convenient double-enzymatic synthesis of both enantiomers of 6-methyl-ε-caprolactone

Both enantiomers of 6-methyl-e-caprolactone (6-MeCL) are obtained in high enantiomeric excess by the combination of an enzymatic ring opening of racemic 6-methyl-e-caprolactone and subsequent enzymatic ring closure. Immobilized Candida antarctica lipase B (Novozym 435) was selected as the biocatalys...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: As, van, B.A.C., Chan, Dah-Kee, Kivit, P.J.J., Palmans, A.R.A., Meijer, E.W.
Format: Article in Journal/Newspaper
Language:English
Published: 2007
Subjects:
Antarc*
Antarctica
Online Access:https://research.tue.nl/en/publications/453bfe1e-b828-47d1-a068-9717ef9f73ff
https://doi.org/10.1016/j.tetasy.2007.03.016
Description
Summary:Both enantiomers of 6-methyl-e-caprolactone (6-MeCL) are obtained in high enantiomeric excess by the combination of an enzymatic ring opening of racemic 6-methyl-e-caprolactone and subsequent enzymatic ring closure. Immobilized Candida antarctica lipase B (Novozym 435) was selected as the biocatalyst for both the ring-opening and the ring-closing reaction. This route provides ready access to enantiopure (S)-6-MeCL (ee = 99.6%) and (R)-6-MeCL (ee = 98.8%).

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