Final Thoughts on Chemistry for (1S,2R)-2-Amino-1,2-diphenylethanol

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Enantioselective addition of benzaldehyde with diethylzinc catalyzed by a few classes of new chiral ligands (3a-3h) and their structural relations are disclosed herein. The stereocontrolled syntheses of both (S)- and (R)-1-phenyl-1-propanol are achieved in high chemical yield (up to 99.3%) with high enantiomeric excess (up to 96.8% e.e) utilizing (1S,2R)-(3a) and (1R,2S)-2-N,N-dimethylamino-1,2-diphenyl ethanol (3b), respectively.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) delta-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active delta-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Iridium(I)-catalysed asymmetric hydrosilylation of ketones using a chiral oxazolylferrocene-phosphine hybrid ligand

The chiral oxazolylferrocene-phosphine hybrid ligand (DIPOF) is a very effective ligand for IrI-catalysed asymmetric hydrosilylation of simple ketones to give the corresponding sec-alcohols (up to 96% ee) after acid hydrolysis.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The cytotoxic agent cell binding receptor conjugate (by machine translation)

[Problem] target for therapy, cell surface receptor binding molecules of strong cytotoxic agent conjugate. (I) having the structure represented by the formula [a] is a pharmaceutically acceptable salt solvent and the conjugate product. In this conjugate is cancer, autoimmune disease or infectious therapy. (T is the target or a binding ligand; L is the dissociation linker; broken line portion L is independently in parentheses structure in the molecule with a link coupling; n is 1 – 20 n; m is 1 – 10 integer, effective anti-mitotic agents in parentheses structures · drug)[Drawing] no (by machine translation)

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Fixed stereochemical control in the synthesis of new mono- and disubstituted 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenes

Five new boronates of the type 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenes (6a-e) were prepared from substituted 2-[(2-hydroxyethylamino)methyl]phenols (4a-e) and phenylboronic acid (5) in benzene-EtOH (4:1) mixtures. Tridentate ligands 4a-e and boronates 6a-e were characterized by 1H, 13C, 15N, and 2D-NMR (HETCOR, NOESY, and COLOC) experiments, FT-IR, mass spectra, and elemental analysis, as well as 11B NMR for the boron derivatives. Suitable monocrystals of 2-[(2-hydroxyethylamino)methyl]phenol hydrochloride (4a), cis-2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononene (6a), (2S,5R,6S)-2,5-diphenyl-6-aza-1,3-dioxa-2-borabenzocyclononene (6b), and (2S,4R,5R,6S)-2,4-diphenyl-5-methyl-6-aza-1,3-dioxa-2-borabenzocyclononene (6e) were obtained and their structures are discussed. The X-ray structures of 6a, 6b, and 6e, as well as the NMR data established that the configurations at the nitrogen and boron atoms are both “S” and the transannular fusion is cis. A semi-empirical (SAM1) study was used to calculate the energy for all possible stereoisomers, showing that the stabilization increases as the THC (tetrahedral character of the boron atom) increases and also as the N?B bond distance decreases, in agreement with the experimental results and previous work related to amino acid boronates.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Brief introduction of (1S,2R)-2-Amino-1,2-diphenylethanol

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Enantiopure azetidine-2-carboxamides as organocatalysts for direct asymmetric aldol reactions in aqueous and organic media

A family of enantiopure azetidine-2-caboxamides was asymmetrically synthesized, and was examined as organocatalyst in direct aldol reactions. A well chosen chiral azetidine-2-caboxamide was found to smoothly catalyze the direct aldol reaction of various benzaldehydes with acetone in brine, and beta-hydroxy ketones were produced with enantiomeric excess up to 96%. The reaction of benzaldehydes with cyclic ketones also led to the formation of anti-products in diastereomeric ratio up to 99:1 and enantiomeric excess up to 99%.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 23364-44-5 is helpful to your research. HPLC of Formula: C14H15NO

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Enantioselective syntheses of beta-amino alcohols catalyzed by recyclable chiral Fe(III) metal complex

An efficient asymmetric desymmetrization of meso-epoxides with anilines catalysed by a series of simple and environmentally benign in situ generated Fe(iii) complexes based on chiral tridentate ligands L1-L7 with achiral and chiral linkers (methylene, piperazine, R/S BINOL and diethyl tartrate) was carried out at rt. The in situ generated iron metal complex based on ligand L5a emerged as improved (low catalyst loading) catalyst for asymmetric desymmetrization of meso-epoxides with anilines giving high enantioselectivity (up to 99%) and high yield (95%) of enantiopure beta-amino alcohols in 14 h. While excellent results for ARO of cyclic as well as aliphatic epoxides with anilines was achieved with in situ generated complex from the ligand L4h and Fe(iii) chloride, the catalyst was recoverable and recyclable (five times) with retention of its performance.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Copper Bis(oxazoline)-Catalyzed Enantioselective Alkynylation of Benzopyrylium Ions

The stereocontrolled construction of biologically relevant chromanones and tetrahydroxanthones has been achieved through the addition of alkynes to benzopyrylium trilfates under the influence of copper bis(oxazoline) catalysis. Excellent levels of enantiocontrol (63?98 % ee) are achieved in the addition of a variety of alkynes to an array of chromenones with a hydrogen in the 2-position. Promising levels of enantiocontrol (54?67 % ee) are achieved in the alkynylation of chromenones with esters in the 2-position, generating tertiary ether stereocenters resembling those frequently found in naturally occurring metabolites.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Copper Bis(oxazoline)-Catalyzed Enantioselective Alkynylation of Benzopyrylium Ions

The stereocontrolled construction of biologically relevant chromanones and tetrahydroxanthones has been achieved through the addition of alkynes to benzopyrylium trilfates under the influence of copper bis(oxazoline) catalysis. Excellent levels of enantiocontrol (63?98 % ee) are achieved in the addition of a variety of alkynes to an array of chromenones with a hydrogen in the 2-position. Promising levels of enantiocontrol (54?67 % ee) are achieved in the alkynylation of chromenones with esters in the 2-position, generating tertiary ether stereocenters resembling those frequently found in naturally occurring metabolites.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Configurational assignment of vic-amino alcohols from their circular dichroism spectra with dirhodium tetracetate as an auxiliary chromophore

The circular dichroism spectra of a variety of vic-amino alcohols in the presence of dirhodium tetraacetate as an auxiliary chromophore were measured in ethanol as the solvent. The method was tested with several model compounds, representing both acyclic and cyclic amino alcohols, including biologically important adrenergic drugs as well as amino sugars. The study demonstrated that the sign of the Cotton effects is determined by the preferred helicity of the O-C-C-N unit in the chiral complex formed in situ. The combined analysis of the CD, UV-vis, 1H and 13C NMR indicated predisposition to form chiral complexes by initial coordination of the amino alcohol at the axial coordination site followed by migration to the equatorial position. Finally, after migration of the ligand to an equatorial position(s) a bridging or a chelating complex is formed. Hence, vic-amino alcohols in ethanol act as bidentate ligands in the end.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI