REACTIONS OF BETA-LACTONES WITH LEWIS-ACIDS - RING ENLARGEMENT VERSUSBETA-ELIMINATION

Authors
MULZER J POINTNER A STRASSER R HOYER K NAGEL U
Citation
J. Mulzer et al., REACTIONS OF BETA-LACTONES WITH LEWIS-ACIDS - RING ENLARGEMENT VERSUSBETA-ELIMINATION, Tetrahedron letters, 36(21), 1995, pp. 3679-3682
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
21
Year of publication
1995
Pages
3679 - 3682
Database
ISI
SICI code
0040-4039(1995)36:21<3679:ROBWL->2.0.ZU;2-L
Abstract
On treatment with MgBr2 tire beta-spirolactones 7 and 10 undergo ring enlargement to the gamma-lactones 8 and 11, whereas the beta-spirolact ones 13 show diastereoselective beta-elimination to form the beta,gamm a-unsaturated acids 14. The Lewis acid influence on the migratory apti tude of Me versus H is studied for beta-lactone 18.