132295-10-4

Upstream product

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

Downstream Products

• 1537890-06-4 diethyl (R)-α-methylbenzylamino-(S)-(2-hydroxyphenyl)methylphosphonate 
• 1537890-28-0 C₁₉H₂₆NO₄P 
• 1537890-15-5 diisopropyl (R)-α-methylbenzylamino-(S)-(2-hydroxyphenyl)methylphosphonate 
• 1537890-29-1 C₂₁H₃₀NO₄P 
• 313963-83-6 N-(2-hydroxybenzyl)-(R)-α-methylbenzylamine 

Relevant academic research and scientific papers

Difference in the rate of photo-induced unimolecular motion of chiral salicylideneamines in the chiral crystal environments

From the kinetic investigation on the photochromic process of chiral N-salicylidene-1-phenylethylamine it was revealed that the rate of unimolecular asymmetric motion was influenced by the neighboring asymmetric crystal environments.

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

New Schiff base zinc(II) complexes exhibiting second harmonic generation

Four bis(salicylaldiminato)zinc(II) complexes have been synthesized from four Schiff bases obtained by the condensation of chiral (R)-(+)-1-phenylethylamine with salicylaldehyde (1), 5-nitrosalicylaldehyde (2), 3,5-dichlorosalicylaldehyde (3) and 5-methox

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.

Kinetic and mechanistic study with optically active, four-coordinate nickel(II) complexes: Stereoselectivity in ligand substitution

Conventional and rapid scan stopped-flow spectrophotometry as well as polarimetry was used to study the kinetics of ligand substitution in six chiral bis N-alkylsalicylaldiminato nickel(II) complexes NiA2 by different chiral salen-type ligands H2B, according to NiA2 + H2B → NiB + 2HA, in acetone at 298 K and, partly, at variable temperature. In most cases ligand substitution was found to follow monophasic second-order kinetics, rate = k x [NiA2] x [H2B]. Second-order rate constant k, lying in the range 10-2 - 400 M-1S-1 at 298 K, was determined for the various combinations of enantiomers in a given system NiA2/H2B, namely, R-NiA2/R-H2B, S-NiA2/R-H2B, R-NiA2/S-H2B, and S-NiA2/S-H2B. It was found that ligand substitution is subject to chiral discrimination. The ratio of second-order rate constants, k(fast)/k(slow), with k(fast) being rate constant k for the faster reacting pair of enantiomers and vice versa, lies in the range 1.0-3.0, depending on the nature of the N-alkyl groups in NiA2 and organic groups attached to the ethylene bridge in the salen ligands H2B. The rate discrimination factor of 3.0, as obtained for NiA2 = bis[N-dehydroabietylsalicylaldiminato]nickel(II) reacting with the R- and with the S-enantiomer of H2B = N,N'-disalicylidene-1,2-diamino-4-methylpentane, appears to be the highest stereoselectivity reported so far for ligand substitution in nickel(II) complexes. With NiA2 = R- and S-bis[N-(1-phenylethyl)-5-nitrosalicylaldiminato]nickel(II) and H2B = R- and S-N,N'-disalicylidene-1,2-diamino-4-methylpentane, the kinetics of ligand substitution are biphasic, describing initial adduct formation between NiA2 and H2B (equilibrium constant K) and stepwise loss of the two bidentate ligands HA (first-order rate constants k1 and k2). The data for K, k1, and k2 for one of the combinations of enantiomers were determined at variable temperature, and the corresponding activation parameters are presented.

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

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.

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.

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