Catalytic oxidation of 4-piperidone-3-carboxylates with manganese(III) acetate in the presence of 1,1-disubstituted alkenes

✍ Scribed by Ryoukou Kumabe; Hiroshi Nishino; Mikio Yasutake; Van-Ha Nguyen; Kazu Kurosawa

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 77 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01884-0

✦ Synopsis

The manganese(III) acetate-catalyzed cycloperoxidation of 4-piperidone-3-carboxylates with 1,1-disubstituted alkenes is described. The 4-piperidone-3-carboxylates reacted with 1,1-disubstituted alkenes in the presence of a catalytic amount of manganese(III) acetate in air at 23°C to give 1-hydroxy-8-aza-2,3-dioxabicyclo[4.4.0]decane-6-carboxylates in good to moderate yields. The crystal structure of the azabicyclic peroxides was determined by an X-ray single crystal analysis. The oxidation of the 4-piperidone-3-carboxylates with 1,1-diphenylethene using a stoichiometric amount of manganese(III) acetate gave ethenyl-and ethyl-substituted 4-piperidones and 6-hydroxy-3-aza-7-oxabicyclo[4.3.0]nonane-1-carboxylate, which was the same as the product obtained from the hydrogenolysis of the 1-hydroxy-8-aza-2,3-dioxabicyclo[4.4.0]decane-6-carboxylate.