A new application about (1R,2S)-(−)-2-Amino-1,2-diphenylethanol

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An optically inactive polyacetylene, poly((4-carboxyphenyl)acetylene) (poly-l), exhibits an induced circular dichroism (ICD) in the UV-visible region upon complexation with chiral amines and amino alcohols in DMSO and in the film, the sign of which reflects the stereochemistry including bulkiness, type (primary, secondary, or tertiary), and absolute configuration of the amines. Therefore, the polyacetylene can be used as a novel probe for determining the chirality of amines. Most primary amines and amino alcohols of the same configuration gave the same sign for the induced Cotton effect; however, secondary and/or tertiary amines used in the present study tended to show Cotton effect signs opposite to those of the primary amines and amino alcohols of the same configuration. The magnitude of the ICD likely increases with an increase in the bulkiness of the chiral amines. The complexation dynamics during the formation of the helical structure of poly-1 with chiral amines were investigated on the basis of the spin-spin relaxation behavior and 1H NMR, CD, and optical rotatory dispersion (ORD) titrations. The complex formation of poly-1 with chiral amines such as 1-(l- naphthyl)ethylamine and 2-amino-l-propanol exhibits a positive nonlinear effect between the enantiomeric excess of the chiral amines and amino alcohols and the observed ellipticity of the Cotton effects. The excess enantiomer bound to poly-1 may induce an excess of a single-handed helix (rightor left-handed helix), which may result in a more intense ICD than that expected from the ee of the amine. Moreover, it was found that the coexistence of achiral amines such as l-aminoethanol also induced an excess of one helical sense of poly-1.

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With the vastly increasing applications of chiral phosphine-oxazoline (PHOX) hybrid ligands in various transition-metal-catalyzed reactions, novel PHOX ligands bearing innovative backbones are highly valuable and in great demand. This study describes the development of a new type of chiral PHOX ligands based on a hexamethyl-1,1?-spirobiindane scaffold and incorporating both a phosphine and an oxazoline moiety. The optimal ligand provided high yields and excellent enantioselectivities for the Ni-catalyzed asymmetric arylation of cyclic N-sulfonyl imines with arylboronic acids leading to chiral amines.

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A series of beta-amino alcohols derived from (1R, 2S)-2-amino-1,2- diphenylethanol and substituted salicylaldehydes as novel chiral tridentate ligands has been applied to an asymmetric Reformatsky reaction of aldehydes with ethyl iodoacetate in the presence of ZnMe2. This novel catalytic system produced the desired beta-hydroxyl esters with moderate to good enantioselectivities (up to 81% ee) and yields for many aldehydes, including aromatic, heteroaromatic, conjugated, and aliphatic aldehydes.

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A series of amino acid-based oxazoline compounds have been prepared and successfully applied to the enantioselective allylation reaction of aldehydes. The fine-tuning of the structure of the oxazolines led to (S,S)-4 as an efficient organocatalyst which gave homoallyl alcohols in good yield (up to 90%) and excellent ee (up to 99%) for a wide range of substrates including aromatic, hetero-aromatic and alpha,beta-unsaturated aldehydes. The chiral organocatalyst was synthesized in three easy steps with an overall 88% yield and successfully recycled for up to three cycles. On the basis of the experimental observations and NMR studies, a probable mechanism was proposed for this reaction.

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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, Application In Synthesis of (1R,2S)-(−)-2-Amino-1,2-diphenylethanol

A three-component Petasis-type gem-difluoroallylation reaction of using pinacol gem-difluoroallylboronates, aldehydes or isatin, and beta-amino alcohols enabled by the neighboring hydroxyl group in amine is reported, affording various racemic and chiral gem-difluorohomoallylamine derivatives with good to excellent results. Based on the control experiment and stereochemistry of the product, a proposed reaction pathway is illustrated to clarify the origin of regio- and stereoselectivity under protic solvent conditions.

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A supramolecular benzothiophene heterocyclic host complex was successfully prepared by combining benzo[b]thiophene-3-acetic acid and chiral (1R,2S)-2-amino-1,2-diphenylethanol. Four types of n-alkyl alcohols could be stored as guests in one-dimensional channel-like cavities composed of 21-helical columnar network structures. The release temperatures of the stored guest alcohols could be multiply tuned according to the type of the benzothiophene unit in the complex. This journal is

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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, Quality Control of: (1R,2S)-(−)-2-Amino-1,2-diphenylethanol

The lipase TL-mediated kinetic resolution of (±)-benzoin (1) proceeded to give the corresponding optically pure benzoin (R)-1. On the other hand, (S)-benzoin-O-acetate (5) could be hydrolyzed without epimerization to give (S)-benzoin (S)-1, under alkaline conditions. Further, (R)-1 was converted to (1R,2S)-2-amino-1,2-diphenylethanol (99:1 er) according to the procedure reported previously. (C) 2000 Elsevier Science Ltd.

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Reference:
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Image Presented An approach that provides symmetrical, unsymmetrical, and asymmetric N-heterocyclic carbene (NHC) ligands is reported. Reaction of iodoethanol with aniline provides N-(2-iodoethyl)arylamine salts that are then converted to the corresponding iodide. Reaction with aliphatic or aromatic amines followed by triethyl orthoformate was used to provide 26 different NHC ligands.

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Chiral Catalysts,
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A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20C to give alpha-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.

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Reference:
Chiral Catalysts,
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The asymmetric alkynylation reaction catalyzed by amino alcohol derived ligands (1R,2S)-3 or (1S,2R)-4 with dimethylzinc provides a simple and practical method to make chiral propargylic alcohols, and it is complementary to the asymmetric reduction methods. In the presence of 10 mol% (1R,2S)-3 or (1S,2R)4, a variety of aromatic aldehydes were converted to the corresponding chiral propargylic alcohols with very good enantioselectivities and yields. This one-pot asymmetric reaction is carried out under mild reaction conditions. Neither strong base nor transmetallation is required. It is an efficient reaction, greatly accelerated by the added chiral ligand. Preliminary mechanistic and NMR studies have also been carried out.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare