Free radical allyl transfers utilizing soluble non-cross-linked polystyrene and carbohydrate scaffold supports
Free radical allylations were studied using (1) soluble non-cross-linked polystyrene supports, (2) carbohydrate scaffolds, and (3) a combination of both synthetic motifs. Allylations on these custom designer supports provide easily purified products, free of tin residues. A D-xylose carbohydrate scaffold bearing a bromoester was used for a diastereoselective allyl tin transfer thermally at 80 degrees C and with Lewis acids. This is the first example of a diastereoselective radical reaction directed by a removable polymer-supported carbohydrate auxiliary.
Enholm
EJ
Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA.
Gallagher
ME
Jiang
S
Batson
WA