| Abstract |
Regio- and stereoselective iodinations under controlled Garegg conditions were performed on vicinal diols and contiguous triols located on pyranose templates. beta-D-Fructo- or psicopyranose-based diols were selectively iodinated at C-5 or C-4, respectively, to afford the L-sorbo or D-tagato iodohydrins. In contrast, the related triols only underwent selective iodination at C-5. Application of the process to D-glucoand D-galactopyranosides resulted in selective iodination at C-3 or C-4, respectively, to afford the D-allo or D-gluco iodohydrins. |
