212073-01-3

Upstream product

• 215321-43-0 Chloro-oxo-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 65253-04-5 (-)-8-phenylmenthol 

Downstream Products

• 212073-04-6 (+)-(1R)-2-benzyl-3-(diphenylmethylidene)-2-azabicyclo[2.2.1]heptane 
• 212073-06-8 (+)-(1R)-2-benzyl-2-azabicyclo[2.2.1]heptan-3-one 
• 192461-74-8 (+)-(1R,3-exo)-2-benzyl-3-[(hydroxy)diphenylmethyl]-2-azabicyclo[2.2.1]heptane 

Relevant academic research and scientific papers

The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction

The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way.