453556-55-3

Upstream product

• 453556-53-1 7,8-dimethoxy-2-(4-methoxy-benzyl)-3,10-dimethyl-3,4-dihydro-2H-benzo[b][1,6]naphthyridin-1-one 
• 453556-45-1 methyl (3S)-3-[N-(p-methoxybenzyl)-N-((ethoxycarbonyl)acetyl)amino]butyrate 
• 453556-46-2 (6S)-1-(p-methoxybenzyl)-6-methylpiperidine-2,4-dione 
• 100-39-0 benzyl bromide 
• 453556-54-2 7,8-dimethoxy-3,10-dimethyl-3,4-dihydro-2H-benzo[b][1,6]naphthyridin-1-one 

Relevant academic research and scientific papers

Influence of the C(4)-C(3)-C=O dihedral angle of chiral NADH mimics on the stereoselectivity of reductions

Herein we report the stereoselective synthesis of new chiral NADH mimics 2 and 13 of the benzo [b]-1,6-naphthryridine series. The synthesis of 2 and 13 relies upon a Friedlander-type condensation between the amino imine 3 and the piperidine-2,4-dione 4 bearing a stereogenic center at C(6). The resulting NADH models were involved in the reduction of methyl benzoylformate. A comparison of their performance with that of previously reported NADH mimics such as model 1, throws new light on the role played by the C(4)-C(3)-C=O dihedral angle (α) on the stereoselectivity of the hydride transfer.