STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED TETRAHYDROFURANS VIA SELENOETHERIFICATION OF 2-SILYL-3-ALKENOLS - A STUDY OF ALLYLIC STEREOCONTROL

Authors
LANDAIS Y PLANCHENAULT D WEBER V
Citation
Y. Landais et al., STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED TETRAHYDROFURANS VIA SELENOETHERIFICATION OF 2-SILYL-3-ALKENOLS - A STUDY OF ALLYLIC STEREOCONTROL, Tetrahedron letters, 36(17), 1995, pp. 2987-2990
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
17
Year of publication
1995
Pages
2987 - 2990
Database
ISI
SICI code
0040-4039(1995)36:17<2987:SSOSTV>2.0.ZU;2-X
Abstract
5-endo-trig selenoetherifications of substituted 2-silyl-3-alkenols ga ve tri- or tetrasubstituted 2,4-cis tetrahydrofurans in moderate to go od yields with excellent diastereoselectivities. Opposite stereoselect ivities were found with an analogous allylic diol. A transition state model has been proposed to rationalize this stereochemical outcome.