Some scientific research about (1R,2S)-(−)-2-Amino-1,2-diphenylethanol

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A Cs-symmetric, rigid, achiral organophosphoric acid host with differentiable tautomeric structures has been developed for induced circular dichroism (ICD) studies of vicinal amino alcohols. The structural features of the host and the substituent bulkiness of the guest, together, decide the preferred mode of hydrogen binding on equilibration with a resultant ICD signal. An unequivocal rule correlating the absolute configuration of the guest amino alcohol with the ICD outcome is proposed.

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l-Pipecolinic acid derived N-formamides have been developed as new Lewis basic organocatalysts that promote the asymmetric reduction of N-aryl ketimines using trichlorosilane as the reducing agent. The substituent on N4 of the piperazinyl backbone and the 2-carboxamide group both proved to have profound effects on the efficacy of the catalyst. The reductions of both N-aryl acyclic methyl ketimines and non-methyl ketimines were catalyzed to afford the desired amines in good to high yield and enantioselectivity. In particular, catalyst 6e enabled the reduction of the difficult bulky ketimines to be highly efficient and enantioselective, affording up to 99% yield and 97% ee. This catalyst proved to prefer the relatively bulkier non-methyl acyclic ketimines to the methyl ketimines as substrate, which is so far unprecedented in catalytic asymmetric reduction of imines.

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Chiral Catalysts,
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Highly enantioselective [4 + 2] cyclizations of azadienes with in situ generated ketenes were developed through sequential visible-light photoactivation/isothiourea catalysis, which offers a novel approach for the creation of all-carbon quaternary stereocenters through disubstituted C1-ammonium enolates. The visible-light-induced sustained release of reactive ketene species through Wolff rearrangement of alpha-diazoketones is crucial for achieving high levels of chemical efficiency and stereoinduction.

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Chiral Catalysts,
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2-(((1R,2S)-2-Hydroxy-1,2-diphenylethylimino)methyl)phenol and 2-(((1S,2R)-2-hydroxy-1,2-diphenylethylimino)methyl)phenol have been synthesized as a pair of enantiomeric Schiff bases of a chiral salicylaldehyde. These compounds were subsequently characterized by melting point, EI-MS, IR, 1H-NMR and X-ray crystallographic analyses. The UV-vis absorption, fluorescent emission, electronic and vibrational circular dichroism (ECD and VCD) spectral properties of these enantiomers were determined in solution in a variety of different solvents, including acetonitrile, ethanol and hexane, as well as being determined in the solid state. The effects of the different solvents were evaluated in detail, and it was found that the enol-imine tautomer existed as the dominant species in nonpolar solvents, such as hexane, and that the enol-imine and keto-enamine tautomers coexisted in polar solvents, such as ethanol. Theoretical IR and VCD spectra of the enantiomers were calculated at the B3LYP/6-311+G(d,p) level by density functional theory. Given that the different tautomers coexisted in solution and VCD is very sensitive to conformational changes, it was not possible to reliably determine the absolute configurations of the enantiomers based on their solution phase VCD spectra. However, the calculated IR and VCD spectra in a vacuum were in good agreement with the experimental solid state spectra, and it was therefore possible to reasonably assign the absolute configurations of the enantiomers based on the VCD calculations. This study therefore represents a good example of the practical application of solid state VCD spectra to assign the absolute configurations of different enantiomers.

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Chiral Catalysts,
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An enantioselective intramolecular cyclization of the bis-phenyllithium species 3 was attained by addition of chiral lithium alkoxides to produce a cyclopenta[b]benzofuran 2 with high % ee’s up to 87 %.

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erythro-2-Amino alcohols (1R,2S)- and (1S,2R)-4 may be synthesized stereoselectively by addition of Grignard compounds to cyanohydrins (R)-, (S)-1 and their O-trimethylsilyl derivatives 3, respectively, followed by hydrogenation.The threo-2-amino alcohols (1S,2S)- and (1R,2R)-4 are easily accessible by inversion at C-1 of the (1R,2S) and (1S,2R) compounds.

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A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 23190-16-1, Name is (1R,2S)-(−)-2-Amino-1,2-diphenylethanol, molecular formula is C6H5CH(NH2)CH(C6H5)OH. In a Conference Paper,once mentioned of 23190-16-1, Quality Control of: (1R,2S)-(−)-2-Amino-1,2-diphenylethanol

The BINOL-amino alcohol enantiomeric pair (S)-1 and (R)-1 are discovered to conduct both enantioselective and diastereoselective fluorescent discrimination of the four stereoisomers of threonine derivatives. This study utilizes different fluorescence responses of one sensor at two emission wavelengths toward the stereoisomeric substrates which expands the capability of the sensor in chiral recognition. In addition, the sensor pair also allows visual recognition of the N-protected l-allo-threonine and d-allo-threonine by enantioselective precipitation.

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Reference:
Chiral Catalysts,
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The present invention discloses a pharmaceutical lesinurad the axle chirality of optical resolution method, the optically active amino alcohol derivatives as resolution agent in the organic solvent with the lesinurad racemate react to form a salt, the salt dissociation, to obtain optically active (R)- or (S)- 2 – (5 – bromo – 4 – (4 – ring propyl naphthalene – 1 – yl) – 4 H – 1, 2, 4 – triazole – 3 – controlling helicobacter) acetic acid. The method of the invention can achieve the ee optical purity 93% more than S configuration of the axle chirality enantiomer and R configuration the axle chirality enantiomer. (by machine translation)

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.23190-16-1, Name is (1R,2S)-(−)-2-Amino-1,2-diphenylethanol, molecular formula is C6H5CH(NH2)CH(C6H5)OH. In a Article,once mentioned of 23190-16-1, Product Details of 23190-16-1

Novel oxazaborolidines B-C6F5 were synthesized by modified protocol from C6F5B(OMe)2 (in place of usual C6F5B(OH)2) and the corresponding amino alcohols, aiming to know the pi-pi stacking and electron-withdrawing effects of C6F5 group in asymmetric reduction of ketones. Although the results were not simply explained by the expected effects, significant difference was observed in the enantioselectivity between the catalysts with B-C6H5 and B-C6F5.

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Chiral Catalysts,
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Direct experimental evidence for the priority of flexible ligand skeleton in asymmetric Friedel-Crafts alkylation was obtained through XRD analysis of flexible ligand/ZnCl2 complex, as well as synthesis of dihydroacridine-linked bis(oxazoline) ligands with planar rigid scaffold. A transition state model without NH phi interaction was proposed for the rigid ligands to interpret the inversion of absolute configuration.

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Reference:
Chiral Catalysts,
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