AN EFFICIENT AND STEREOSELECTIVE CONVERSION OF LACTONES TO SUBSTITUTED CYCLIC ETHERS

Authors
YODA H MIZUTANI M TAKABE K
Citation
H. Yoda et al., AN EFFICIENT AND STEREOSELECTIVE CONVERSION OF LACTONES TO SUBSTITUTED CYCLIC ETHERS, Heterocycles, 48(4), 1998, pp. 679-686
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
48
Issue
4
Year of publication
1998
Pages
679 - 686
Database
ISI
SICI code
0385-5414(1998)48:4<679:AEASCO>2.0.ZU;2-Q
Abstract
A general route to substituted cyclic ethers has been described by usi ng nucleophilic addition of Grignard reagents to lactones in the prese nce of CeCl3 followed by the Lewis acid-induced deoxygenation of the c orresponding hemiketals with Et3SiH. Stereoselective reduction of the 5-membered adducts to the disubstituted tetrahydrofurans has been also investigated.