Diketopiperazine-derived hydroperoxide for chemoselective oxidations of sulfides and enantioselective Weitz–Scheffer epoxidations

✍ Scribed by Marcel Kienle; Wassiliki Argyrakis; Angelika Baro; Sabine Laschat

• Book ID: 104095016
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 124 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.01.090

✦ Synopsis

L-Proline-derived hydroperoxide (À)-2, which was obtained from the corresponding diketopiperazine by irradiation under oxygen atmosphere, was applied to the oxidation of a variety of sulfides and asymmetric Weitz-Scheffer epoxidations of cyclic and acyclic enones. The sulfoxidation, however, gave only racemic products. In contrast, depending on the base catalyst, enantioselectivities up to 37% were achieved in the epoxidation of chalcone with (À)-2.