354147-45-8

Upstream product

• 50-00-0 formaldehyd 
• 313963-79-0 1-((R)-phenyl-(((R)-1-phenylethyl)amino)methyl)naphthalen-2-ol 
• 100-52-7 benzaldehyde 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 135-19-3 β-naphthol 

Downstream Products

• 479578-14-8 {(R)-[2-(di-p-tolylphosphinoyl)naphthalen-1-yl](phenyl)methyl}methyl((1R')-1'-phenylethyl)amine 
• 479578-08-0 {(R)-[2-(diphenylphosphinoyl)naphthalen-1-yl](phenyl)methyl}methyl((1R')-1'-phenylethyl)amine 
• 479578-07-9 1-{(R)-[N-methyl-((1'R)-1'-phenylethyl)amino](phenyl)methyl}naphthalen-2-yl trifluoromethanesulfonate 
• 479578-05-7 1-{(R)-[N-methyl-((1'R)-1'-phenylethyl)amino](phenyl)methyl}naphthalen-2-ol 

Relevant academic research and scientific papers

Synthesis of a new type of chiral amino phosphine ligands for asymmetric catalysis

This article describes the synthesis of a new type of chiral amino phosphine ligands from an amino naphthol starting material derived by asymmetric 1-aminoalkylation of 2-naphthol with (R)-1-phenylethylamine and benzaldehyde. The asymmetric induction properties of the ligands in the Pd(0)-catalyzed allylic substitution of 1,3-diphenylprop-2-en-1-yl acetate with dimethyl malonate has also been investigated, with near-quantitative yields and ee of up to 72.2% of the product being obtained under the optimized reaction conditions.

A practical stereoselective synthesis of secondary and tertiary aminonaphthols: Chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde

A practical procedure for the stereoselective synthesis of a wide group of functionalized aminoalkylnaphthols, using inexpensive starting materials, is reported. Selective N-alkylation was carried out by cyclization of secondary aminoalkylnaphthols with formaldehyde, followed by reduction or alkylation with organometallic reagents. The catalytic activity of this class of compounds was tested in the addition of diethylzinc to benzaldehyde, resulting in moderate to good enantioselectivities. It is noteworthy that the aminonaphthols obtained as the major diastereomer in the solvent free synthesis, have the best asymmetric induction properties in the alkylation reaction.

Ready N-alkylation of enantiopure aminophenols: Synthesis of tertiary aminophenols

A regioselective indirect alkylation of aminophenols to enantiopure tertiary aminophenols, which are useful chiral ligands for metal-catalysed asymmetric reactions, is reported. This very simple synthetic methodology, through reduction or alkylation of an intermediate benzoxazine, was performed in mild conditions, suitable for the conservation of the configuration of the stereogenic centres. Some crystalline aminophenols show the phenomenon of 'crystallization-induced asymmetric transformation'.

Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: Stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation

Electron-rich aromatic compounds such as 2-naphthol give a faster and asymmetric 1-aminoalkylation with high yields when treated with (R)-1-phenylethylamine and aromatic aldehydes in solvent-free conditions. An asymmetric transformation of a second kind, probably induced by the preferential crystallization of one diastereomer, affords the straightforward and stereoselective synthesis of aminoalkylnaphthols. Mechanisms predictable for this asymmetric reaction are reported. The absolute configurations and the conformations of the unknown aminonaphthols are widely ascertained.