Synthesis and reactions of amino acid-derived benziodazole oxides: new chiral oxidizing reagents

The novel benziodazole oxides (3) can be prepared by oxidation of the readi ly available 2-iodobenzamides (5 or 6) with potassium bromate. Benziodazole oxides can find practical application as selective oxidizing reagents anal ogous to the widely used Dess-Martin periodinane (1) and benziodoxole oxide (2). Preliminary results indicate that reagents 3 can oxidize primary alco hols to aldehydes, while non-symmetric sulfides are oxidized to chiral sulf oxides with moderate enantioselectivity. (C) 2000 Published by Elsevier Sci ence Ltd.