Title of article
Thermodynamics versus kinetics in hetero-Michael cyclizations: a highly stereoselective approach to access both epimers of a C-d-mannopyranoside
Author/Authors
Aucagne، نويسنده , , Vincent and Tatibouët، نويسنده , , Arnaud and Rollin، نويسنده , , Patrick، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2008
Pages
4
From page
4750
To page
4753
Abstract
A simple method for the stereocontrolled synthesis of both α and β pseudo-anomers of a thio-functionalized C-glycoside is described. A 2,3:4,6-di-O-isopropylidene manno scaffold is employed to allow a strict control of the diastereoselectivity of the base-catalyzed intramolecular hetero-Michael addition of an alcohol to a vinyl sulfone, by simply changing the temperature of the reaction.
Keywords
Michael addition , vinyl sulfone , C-glycoside , Vinyl sulfoxide , carbohydrate
Journal title
Tetrahedron Letters
Serial Year
2008
Journal title
Tetrahedron Letters
Record number
1860460
Link To Document