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 readily available 2-iodobenzamides (5 or 6) with potassium bromate. Benziodazole oxides can find practical application as selective oxidizing reagents analogous to the widely used Dess–Martin periodinane (1) and benziodoxole oxide (2). Preliminary results indicate that reagents 3 can oxidize primary alcohols to aldehydes, while non-symmetric sulfides are oxidized to chiral sulfoxides with moderate enantioselectivity.