347381-75-3

Upstream product

• 347381-71-9 (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carboxylic acid methyl ester 
• 347381-79-7 (1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate 
• 130195-74-3 (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid methyl ester 
• 347381-84-4 [(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-((S)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]dec-9-yl]-methanol 

Downstream Products

• 347381-78-6 (R)-1-[(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-((S)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]dec-9-yl]-ethanol 
• 347381-76-4 1-[(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-aza-tricyclo[5.2.0^2,6]dec-9-yl]ethanone 

Relevant academic research and scientific papers

Remote dipole effects as a means to accelerate [Ru(amino alcohol)]catalyzed transfer hydrogenation of ketones

A new generation of 2-azanorbornyl amino alcohol ligands for the catalytic transfer hydrogenation reaction of aromatic ketones was synthesized. Extremely active catalysts were formed by introducing a ketal functionality at the rear end of the ligand. Acetophenone was reduced in 96% ee at low catalyst loading, substrate to catalyst ratio, S/C 5000, within 90 minutes with isopropyl alcohol as the hydrogen donor. It was found that the dioxolane substituent in the ligand increased the turnover frequency, TOF50, from 1050 h-1 to 3000 h-1 at an S/C ratio of 1000. Introduction of a methyl group at the carbinol carbon resulted in TOF50 as high as 8500 h-1. Transfer hydrogenation of a range of aromatic ketones was evaluated and found to reach completion within 30 minutes at room temperature, and excellent enantioselectivity, up to 99% ee, was obtained. A possible explanation for the enhanced activity was provided by density functional calculations, which showed that the presence of a remote dipole in the ligand lowered the transition state energy.