321917-76-4

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 123-11-5 4-methoxy-benzaldehyde 
• 618-36-0 rac-methylbenzylamine 
• 98-84-0 (+)-α-methylbenzylamine 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 960160-82-1 (1'R,2R,3R)-1-(1'-phenylethyl)-2-(4-methoxyphenyl)-3-hydroxyazetidine 
• 960160-83-2 (1'R,2S,3S)-1-(1'-phenylethyl)-2-(4-methoxyphenyl)-3-hydroxyazetidine 
• 1422542-35-5 C₁₆H₁₇NO₂ 
• 2912-98-3 (R)-1-Phenylethylhydroxylamine 
• 1380113-87-0 C₂₀H₂₃NO₃ 
• 209164-43-2 C₂₀H₂₃NO₃ 

Relevant academic research and scientific papers

Stereochemical analysis of chiral amines, diamines, and amino alcohols: Practical chiroptical sensing based on dynamic covalent chemistry

Practical chiroptical sensing with a small group of commercially available aromatic aldehydes is demonstrated. Schiff base formation between the electron-deficient 2,4-dinitrobenzaldehyde probe and either primary amines, diamines, or amino alcohols proceeds smoothly in chloroform at room temperature and is completed in the presence of molecular sieves within 2.5 hours. The substrate binding coincides with a distinct circular dichroism signal induction at approximately 330 nm, which can be correlated to the absolute configuration and enantiomeric composition of the analyte. The usefulness of this sensing method is highlighted with the successful sensing of 18 aliphatic and aromatic amines and amino alcohols and five examples showing quantitative %ee determination with good accuracy.

One-Pot Catalytic Approach for the Selective Aerobic Synthesis of Imines from Alcohols and Amines Using Efficient Arene Diruthenium(II) Catalysts under Mild Conditions

A green and efficient catalytic approach for the selective synthesis of imines in air at room temperature was achieved with the aid of newly synthesised diruthenium(II) complexes [(η6-p-cymene)2Ru2Cl2(μ-L)] containing substituted 1,2-diacylhydrazine ligands. All the new complexes were fully characterised by analytical and spectroscopic techniques. The solid-state structure of a representative complex was solved by single-crystal X-ray diffraction analysis. The diruthenium(II) complexes also enable the selective aerobic oxidation of alcohols to aldehydes. The catalytic reaction operates in the presence of air as a green and cheap oxidant, and releases water as the only by-product. A plausible mechanism is proposed for the imine formation, which is believed to proceed via an aldehyde intermediate.

Asymmetric induction in the addition of enantiomerically pure H-phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P,C-stereogenic centers

α-Amino phosphinates with P,C-stereogenic centers were prepared from a P-retained addition of (RP)-(?)-menthyl H-phenylphosphinate to (R)-aldimines with up to 86:14 dr under catalyst and solvent free condition at ambient temperature; the single

A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by 1H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines

The catalytic asymmetric aziridination of imines and diazo compounds (AZ reaction) mediated by boroxinate catalysts derived from the VANOL and VAPOL ligands was investigated with chiral imines derived from five different chiral, disubstituted, methyl amines. The strongest matched and mismatched reactions with the two enantiomers of the catalyst were noted with disubstituted methyl amines that had one aromatic and one aliphatic substituent. The synthetic scope for the AZ reaction was examined in detail for α-methylbenzyl amine for cis-aziridines from α-diazo esters and for trans-aziridines from α-diazo acetamides. Optically pure aziridines could be routinely obtained in good yields and with high diastereoselectivity and the minor diastereomer (if any) could be easily separated. The matched case for cis-aziridines involved the (R)-amine with the (S)-ligand, but curiously, for trans-aziridines the matched case involved the (R)-amine with the (R)-ligand for imines derived from benzaldehyde and n-butanal, and the (R)-amine with the (S)-ligand for imines derived from the bulkier aliphatic aldehydes pivaldehyde and cyclohexane carboxaldehyde.

Chiral oxaziridines in the enantioselective synthesis of isoxazolidines

The stereoselective synthesis of oxaziridines with three stereogenic centres is presented in this paper. The chirality is provided by asymmetric induction, and a possible mechanism for the induced stereoselectivity is also discussed. These small heterocyc

Synthesis of new chiral cis-3-hydroxyazetidines and their application in diethylzinc addition to aldehydes

A new series of chiral cis-3-hydroxyazetidines have been prepared from (R)-1-phenylethylamine. They have excellent catalytic activities and enantiomeric selectivities in asymmetric addition of diethylzinc to aromatic aldehydes.

A new protocol for the one-pot preparation of highly diastereomerically enriched secondary amines and β-amino esters mediated by lithium perchlorate solution in diethyl ether

A highly diastereoselective one-pot, three-component method for the preparation of several secondary amines and amino esters is reported. Treatment of aldehydes (aliphatic or aromatic) with chiral amines and functionalized organozinc reagents (e.g. BrZnCH