Reaction of quinine, 9-epiquinine and their acetates in superacid in the presence of hydrogen peroxide: an access to new fluorhydrins and/or ketones

In HF–SbF5, in the presence of H2O2 (source of OH+ equivalent) quinine 1a yields 10-keto derivatives 4a and 5a and cyclic ether 3 as the major product. In the same conditions 1b, 2a, and 2b give the 10-keto and 10-fluoro-3-hydroxy analogs.