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

作者: Ryoukou Kumabe , Hiroshi Nishino , Mikio Yasutake , Van-Ha Nguyen , Kazu Kurosawa

DOI: 10.1016/S0040-4039(00)01884-0

关键词: Crystal structureHydrogenolysisMedicinal chemistryCatalysisSingle crystalChemistryManganeseCatalytic oxidationManganese(III) acetateStoichiometry

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

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