Conformation of Glycosyl Radicals: Radical Stabilization by β-CO Bonds (pages 896–898)
Jacques Dupuis, Prof. Dr. Bernd Giese, Daniel Rüegge, Prof. Dr. Hanns Fischer, Dr. Hans-Gert Korth and Prof. Dr. Reiner Sustmann
Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198408961
A transformation from the chair- into the boat conformation takes place when glucosides such as 1 are converted into glucosyl radicals 2. This preference for the boat conformation is due to the radical-stabilizing effect of the coplanar arrangement of the β-CO bond and semi-occupied orbital. The findings are of interest regarding stereoselective radical CC-linkage in the synthesis of C-glycosides.