Zinc-mediated reductive ring opening

After establishing general reaction conditions for the zinc-mediated reductive ring-opening-allylation of iodoglycosides, Madsen et al. developed a similar procedure for the domino reaction of methyl 5-deoxy-5-iodo-pentofuranosides with propargyl... 

Fiirstner reported that organic azides influence the zinc-induced ring-opening reactions of deoxyhalogenosugars. This effect is equally effective intra- and intermolecularly (Scheme 8.38) and it is assumed that the presence of an alky azides favors a radical mediated reduction over the formation of an organozinc species. 

---