180406-57-9

Upstream product

• 72761-60-5 9-azabicyclo<3.3.1>nonan-3-one hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 542-05-2 acetonedicarboxylic acid 
• 4390-39-0 9-azabicyclo[3.3.1]nonan-3-one 

Downstream Products

• 180406-45-5 (1R,5S)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene 
• 180580-54-5 (1S,5R)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene 
• 35986-02-8 N-p-toluenesulfonyl-6-oxa-2-azaadamantane 
• 37073-23-7 N,N′-di-p-toluenesulfonyl-2,6-diazaadamantane 
• 180406-51-3 (1R,2R,3S,4S,6S)-3-Methyl-10-(toluene-4-sulfonyl)-4-trimethylsilanyloxy-10-aza-tricyclo[4.3.1.0^2,4]decane 
• 180580-52-3 (1R,2R,3R,4S,6S)-3-Methyl-10-(toluene-4-sulfonyl)-4-trimethylsilanyloxy-10-aza-tricyclo[4.3.1.0^2,4]decane 
• 180406-53-5 methyl (2R,6S)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate 
• 225089-42-9 methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate 
• 180406-54-6 (2R,6S)-6-formylmethyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 
• 225089-43-0 (2S,6R)-6-formylmethyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 
• 225089-40-7 (1S,2S,3R,4R,6R)-4-hydroxy-3-methyl-N-(p-tolylsulfonyl)-10-azatricyclo<4.3.1.0^2,4>decane 
• 180406-52-4 (1R,2R,3S,4S,6S)-4-hydroxy-3-methyl-N-(p-tolylsulfonyl)-10-azatricyclo<4.3.1.0^2,4>decane 
• 117941-17-0 (2R,6R)-6-Methyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 

Relevant academic research and scientific papers

Mechanistic insight into aerobic alcohol oxidation using NOx-nitroxide catalysis based on catalyst structure-activity relationships

The mechanism of an NOx-assisted, nitroxide(nitroxyl radical)-catalyzed aerobic oxidation of alcohols was investigated using a set of sterically and electronically modified nitroxides (i.e., TEMPO, AZADO (1), 5-F-AZADO (2), 5,7-DiF-AZADO (3), 5-MeO-AZADO (4), 5,7-DiMeO-AZADO (5), oxa-AZADO (6), TsN-AZADO (7), and DiAZADO (8)). The motivation for the present study stemmed from our previous observation that the introduction of an F atom at a remote position from the nitroxyl radical moiety on the azaadamantane nucleus effectively enhanced the catalytic activity under typical NOx-mediated aerobic-oxidation conditions. The kinetic profiles of the azaadamantane-N-oxyl-[AZADO (1)-, 5-F-AZADO (2)-, and 5,7-DiF-AZADO (3)]-catalyzed aerobic oxidations were closely investigated, revealing that AZADO (1) showed a high initial reaction rate compared to 5-F-AZADO (2) and 5,7-DiF-AZADO (3); however, AZADO-catalyzed oxidation exhibited a marked slowdown, resulting in ～90% conversion, whereas 5-F-AZADO-catalyzed oxidation smoothly reached completion without a marked slowdown. The reasons for the marked slowdown and the role of the fluoro group are discussed. Oxa-AZADO (6), TsN-AZADO (7), and DiAZADO (8) were designed and synthesized to confirm their comparable catalytic efficiency to that of 5-F-AZADO (2), providing supporting evidence for the electronic effect on the catalytic efficiency of the heteroatoms under NOx-assisted aerobic-oxidation conditions.

Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent λ(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps.