78419-84-8

Upstream product

• 133603-83-5 (HOC₆H₄CHN)2CH₂CHCH₂CH(CH₃)2 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 271-95-4 1,2-benzisoxazole 
• 72519-00-7 (1R,2S,3S,5R)-N-(α-phenylethylamino)ephedrine 
• 72580-52-0 N-(benzylideneamino)ephedrine 
• 89-95-2 2-methyl-benzyl alcohol 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 90-02-8 salicylaldehyde 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 223268-39-1 2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)butyl>phenol 
• 223268-73-3 2-<(1R)-phenyl-(<(1'R)-1'-phenylethyl>amino)methyl>phenol 
• 223269-26-9 2-<(1S)-phenyl-(<(1'R)-1'-phenylethyl>amino)methyl>phenol 
• 254096-79-2 3-[(1R)-1-phenylethyl]-3,4-dihydro-2H-1,3-benzoxazine 

Relevant academic research and scientific papers

Heteroleptic enantiopure Pd(ii)-complexes derived from halogen-substituted Schiff bases and 2-picolylamine: Synthesis, experimental and computational characterization and investigation of the influence of chirality and halogen atoms on the anticancer acti

Seven enantiomeric pairs of palladium complexes, [Pd(pic)(R or S)-N-1-(phenyl)ethyl-2,4-X1,X2-salicylaldiminate)]NO3, [Pd(pic)(R or S)]NO3 (X1 = X2 = Cl, Br, I, H; X1/X2 = Br/Cl), were synthesized by the reaction of enantiopure halogen-substituted Schiff

A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination

A mild and practical method for the catalytic installation of the amino group across alkenes and alkynes has long been recognized as a significant challenge in synthetic chemistry. As the direct hydroamination of olefins using ammonia requires harsh conditions, the development of suitable electrophilic aminating reagents for formal hydroamination methods is of importance. Herein, we describe the use of 1,2-benzisoxazole as a practical electrophilic primary amine source. Using this heterocycle as a new amino group delivery agent, a mild and general protocol for the copper-hydride-catalyzed hydroamination of alkenes and alkynes to form primary amines was developed. This method provides access to a broad range of chiral α-branched primary amines and linear primary amines, as demonstrated by the efficient synthesis of the antiretroviral drug maraviroc and the formal synthesis of several other pharmaceutical agents.

Aggregation-induced emission enhancement of chiral boranils

New boranils based on chiral benzylamines have been synthesized and their photophysical properties studied. These BF2-complexes exhibit a bright blue fluorescence in solution and in the solid state, and exhibit aggregation-induced emission enhancement. The chirality of the ligand, even if it is not directly located at the boron center, has consequences on the circular dichroism of the complexes.

Synthesis, characterization and crystal structures of ruthenium complexes with bidentate chiral salicylaldiminato ligands

Condensations of salicylaldehyde and 4-chlorosalicylaldehyde with (R)-α-methylbenzylamine in refluxing ethanol afforded the chiral Schiff base ligands (R)-N-(1-phenylethyl)salicylidene (HL1?) and (R)-N-(1-phenylethyl)(4-chlorosalicylidene) (HL2?), respectively. Similarly, reaction of 3,5-di-tert-butylsalicylaldehyde and (S)-2-amino-3-methylbutan-1-ol gave the chiral Schiff base ligand (S)-N-(1-hydroxymethylisobutyl)(3,5-di-tert-butylsalicylidene) (HL3?). Treatment of (Et4N)[RuCl4(MeCN)2] and [RuCl3(NO)(PPh3)2] with HL1? in the presence of triethylamine afforded an anionic ruthenium(III) complex (R,R)-(Et4N)[Ru(κ2-N,O-L1?)2Cl2] (1) and a neutral ruthenium(II) nitrosyl complex (R)-[Ru(κ2-N,O-L1?)(NO)Cl2(PPh3)] (2), respectively. Interaction of [RuCl2(PPh3)3] and 2 equiv. HL2? led to isolation of a ruthenium(III) complex (R,R)-[Ru(κ2-N,O-L2?)2Cl(PPh3)] (3). Reaction of [Ru(NO)Cl3·xH2O] and HL3? gave an anionic ruthenium(II) nitrosyl complex (S)-(Et3NH)[Ru(κ2-N,O-L3?)(NO)Cl3] (4). The molecular structures of ligands HL1? HL2? and ruthenium complexes 1–4 have been determined by single-crystal X-ray crystallography.

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

Stereoselective addition of dialkyl phosphites to di-salicylaldimines bearing the (R,R)-1,2-diaminocyclohexane moiety

The addition of dialkyl phosphites to the azomethine bond of N,N′-disalicylidene-1,2-diaminocyclohexane imines, catalyzed by sodium hydride led to bis-aminophosphonates in a high diastereoselectivity. One of the bis-aminophosphonates was analyzed by X-ray

Chiroptical inversion induced by rotation of a carbon-carbon single bond: An experimental and theoretical study

We propose a new strategy to construct chiral molecular switches with highly reversible and sensitive chiroptical responses to variations in the external environment. Its fundamental concept involves a stimuli-triggered exchange of two conformations presenting significantly different chiroptical properties through the rotation of a carbon-carbon single bond, as demonstrated by chiral Schiff bases s-1, s-2, and a salicylamide analogue s-3. Upon addition of base in solution, the circular dichroism (CD) spectra of these molecular switches displayed unique changes featuring an inversion of the Cotton effect's signs, and the original CD profiles can be recoverd by acidification. Various spectroscopic studies as well as the conformational analysis combining with TDDFT computations allowed clear elucidation of the chiroptical inversion mechanism. It is expected that this kind of chiroptical switches is of great interest for molecular recognition, chemosensing, and the construction of molecular-scale devices. Furthermore, the present study indicates that the use of the conformational transition about a single bond may serve as the basis for designing chiroptical inversion systems.

Design of chiral sulfoxide-Schiff base hybrids and their application in Cu-catalyzed asymmetric Henry reactions

A new class of chiral sulfoxide-Schiff base ligands has been developed by the rational combination of two privileged chiral backbones. These sulfoxide-Schiff base ligands were found to be highly efficient for Cu-catalyzed asymmetric Henry reactions (up to

Chiral discrimination asserted by enantiomers of Ni (II), Cu (II) and Zn (II) Schiff base complexes in DNA binding, antioxidant and antibacterial activities

Chiral Schiff base ligands (S)-H2L and (R)-H2L and their complexes (S-Ni-L, R-Ni-L, S-Cu-L, R-Cu-L, S-Zn-L and R-Zn-L) were synthesized, characterized and examined for their DNA binding, antioxidant and antibacterial activities. The

Rapid, in situ synthesis of bidentate ligands: Chromatography-free generation of catalyst libraries

The parallel synthesis of chiral bidentate ligands and their subsequent use in situ for a catalytic process is described. The ligands thus prepared gave comparable results to those obtained when the ligands were synthesized and purified by conventional means. This includes oxazolines and other compounds of similar complexity, meaning that for the first time these valuable compounds have been brought into the field of combinatorial catalysis.