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Optically active 6-acetyloxy-2H-pyran-3(6H)-one obtained by lipase catalyzed transesterification and esterification

✍ Scribed by Marco van den Heuvel; Agnes D. Cuiper; Hanneke van der Deen; Richard M. Kellogg; Ben L. Feringa

Book ID: 104256528
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 234 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00155-x

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✦ Synopsis

Kinetic resolution of 6-acetyloxy-2H-pyran-3(6H)-one (1) is achieved by immobilized lipase PS on Hyflo Super Cell in organic solvents. Transesterification in hexane/n-butanol yields enantiomerically pure R-(-)-6-acetyinxy-2H-pyran-3(6H)-one, whereas esterification of 6-hydroxy-2H-pyran-3(6H)-one (2) with vinyl acetate by immobilized lipase PS gives the S-cnantiomer with e.e.'s up to 76%.

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