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. 2000 Oct 19;2(21):3355-7.
doi: 10.1021/ol006449e.

Free radical allyl transfers utilizing soluble non-cross-linked polystyrene and carbohydrate scaffold supports

EJ Enholm  1 , ME Gallagher, S Jiang, WA Batson
Affiliations

Free radical allyl transfers utilizing soluble non-cross-linked polystyrene and carbohydrate scaffold supports

EJ Enholm et al. Org Lett. .

Abstract

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.

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