180406-52-4

Upstream product

• 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 
• 594-02-5 1,1-diiodoethane 
• 180406-45-5 (1R,5S)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene 
• 180406-57-9 N-p-tolylsulfonyl-9-azabicyclo<3.3.1>nonan-3-one 

Downstream Products

• 180406-53-5 methyl (2R,6S)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate 
• 501-02-0 (-)-pinidine 
• 117941-17-0 (2R,6R)-6-Methyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 
• 180406-54-6 (2R,6S)-6-formylmethyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 

Relevant academic research and scientific papers

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.

Efficient synthesis of an enantiomeric pair of pinidine: An illustration of organochemical carving on the rigid bridged system as the stereochemical tactics

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 iodoid as key steps.