1027153-74-7

Upstream product

• 454229-02-8 (1S,2S,5R)-2-Phenyl-6-aza-bicyclo[3.2.2]nona-3,8-diene-4,6-dicarboxylic acid 4-methyl ester 6-phenyl ester 
• 119987-21-2 (E)-methyl 2-diazo-4-phenylbut-3-enoate 
• 79328-86-2 1-(phenoxycarbonyl)-1,2-dihydropyridine 

Relevant academic research and scientific papers

Rhodium carboxylate catalyzed decomposition of vinyldiazoacetates in the presence of heterodienes: Enantioselective synthesis of the 6-azabicyclo[3.2.2]nonane and 6-azabicyclo[3.2.2]nonanone ring systems

Dirhodium tetracarboxylate catalyzed decomposition of vinyldiazoacetates in the presence of N-phenoxycarbonyl protected 1,2-dihydropyridines or 1-methyl-2-pyridones is a direct method for the construction of the 6-azabicyclo[3.2.2]nonane ring system. The [3 + 4] cycloaddition occurs by a tandem cyclopropanation/Cope rearrangement. Asymmetric induction is possible in these transformations either by using (S)-lactate methyl ester as a chiral auxiliary or dirhodium tetraprolinates as chiral catalysts.