Enzymatic desymmetrization of meso cis,cis-2,4,6-substituted tetrahydropyrans

Authors
Chenevert, R Goupil, D Rose, YS Bedard, E
Citation
R. Chenevert et al., Enzymatic desymmetrization of meso cis,cis-2,4,6-substituted tetrahydropyrans, TETRAHEDR-A, 9(24), 1998, pp. 4285-4288
Citations number
7
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
9
Issue
24
Year of publication
1998
Pages
4285 - 4288
Database
ISI
SICI code
0957-4166(199812)9:24<4285:EDOMCT>2.0.ZU;2-D
Abstract
The stereoselective acylation of meso-tetrahydropyrans 6 and 7 by enol eate rs (vinyl acetate or isopropenyl acetate) in the presence of Candida antarc tica lipase in organic media gave the corresponding (2R,4S,6S)monoesters 10 and 11 in high enantiomeric purity. The hydrolysis of the corresponding di acetate derivatives 8 and 9 in the presence of the same enzyme provided the opposite enantiomers, (2S,4R,6R)-monoesters 10 and 11. (C) 1998 Elsevier S cience Ltd. All rights reserved.