OPTICALLY-ACTIVE 6-ACETYLOXY-2H-PYRAN-3(6H)-ONE OBTAINED BY LIPASE-CATALYZED TRANSESTERIFICATION AND ESTERIFICATION

Authors
VANDENHEUVEL M CUIPER AD VANDERDEEN H KELLOGG RM FERINGA BL
Citation
M. Vandenheuvel et al., OPTICALLY-ACTIVE 6-ACETYLOXY-2H-PYRAN-3(6H)-ONE OBTAINED BY LIPASE-CATALYZED TRANSESTERIFICATION AND ESTERIFICATION, Tetrahedron letters, 38(9), 1997, pp. 1655-1658
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
9
Year of publication
1997
Pages
1655 - 1658
Database
ISI
SICI code
0040-4039(1997)38:9<1655:O6OBL>2.0.ZU;2-F
Abstract
Kinetic resolution of 6-acetyloxy-2H-pyran-3(6H)-one (1) is achieved b y immobilized lipase PS on Hyflo Super Cell in organic solvents. Trans esterification in hexane/n-butanol yields enantiomerically pure R-(-)- 6-acetyloxy-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-enantiomer with e.e.'s up to 76%. (C) 1997 Elsevier Science Ltd .