New explortion of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Optical Chirality Sensing with a Stereodynamic Aluminum Biphenolate Probe

The determination of the enantiopurity and the concentration of chiral compounds by chiroptical sensing with molecular probes is increasingly attractive for high-throughput screening applications including streamlined asymmetric reaction development. In this study, we use stereodynamic aluminum biphenolate complexes for quantitative ee and concentration analysis of amino alcohols and alpha-hydroxy acids. An important feature of the tropos biphenolate ligand used is the presence of phenylacetylene antennae for optimal chirality recognition and CD/UV responses at high wavelengths. The complexation-driven chirality amplification yields strong CD signals which allows quantitative chiroptical sensing with good accuracy. We show that aluminate biphenolate sensors can exhibit linear and nonlinear correlations between the induced CD signals and the enantiomeric composition or concentration of the chiral substrate.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Synthesis, X-ray analysis, and biological evaluation of a new class of stereopure lactam-based HIV-1 protease inhibitors

In an effort to identify a new class of druglike HIV-1 protease inhibitors, four different stereopure beta-hydroxy gamma-lactam-containing inhibitors have been synthesized, biologically evaluated, and cocrystallized. The impact of the tether length of the central spacer (two or three carbons) was also investigated. A compound with a shorter tether and (3R,4S) absolute configuration exhibited high activity with a Ki of 2.1 nM and an EC50 of 0.64 muM. Further optimization by decoration of the P1? side chain furnished an even more potent HIV-1 protease inhibitor (Ki = 0.8 nM, EC50 = 0.04 muM). According to X-ray analysis, the new class of inhibitors did not fully succeed in forming two symmetric hydrogen bonds to the catalytic aspartates. The crystal structures of the complexes further explain the difference in potency between the shorter inhibitors (two-carbon spacer) and the longer inhibitors (three-carbon spacer).

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Titanium complexes containing tridentate [ONO] type Schiff base ligands for the cycloaddition reaction of CO2 to propylene oxide

New titanium complexes, TiLCl2(THF) and TiL2, containing the tridentate chiral Schiff-base ligand, L, prepared from the condensation reaction of 2,4-pentadione and (1R,2S)-(?)-1-aminoindanol, were synthesized and characterized by various analytical methods including X-ray crystallography. Ligand L acted as a dianionic tridentate ligand and, owing to a chiral center in the aminoindanol part, imparted chirality to its titanium complexes. The newly synthesized titanium complexes and previously reported analogous Ti complexes were used as catalysts in the cycloaddition of CO2 to propylene oxide as the first representatives of titanium complexes with tridentate Schiff base ligands to have been used for this purpose. These complexes provided high selectivity toward cyclic propylene carbonate (>99%) and showed considerable activities with TOF values up to 131 h?1 in comparison with the previously reported catalyst systems.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Readily Accessible and Highly Efficient Ferrocene-Based Amino-Phosphine-Alcohol (f-Amphol) Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of Simple Ketones

We have successfully developed a series of novel and modular ferrorence-based amino-phosphine-alcohol (f-Amphol) ligands, and applied them to iridium-catalyzed asymmetric hydrogenation of various simple ketones to afford the corresponding chiral alcohols with excellent enantioselectivities and conversions (98?99.9 % ee, >99 % conversion, turnover number up to 200 000). Control experiments and density functional theory (DFT) calculations have shown that the hydroxyl group of our f-Amphol ligands played a key role in this asymmetric hydrogenation.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Synthetic Route of 126456-43-7, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.126456-43-7, Name is (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol, molecular formula is C9H11NO. In a article£¬once mentioned of 126456-43-7

Lipases in asymmetric transformations: Recent advances in classical kinetic resolution and lipase?metal combinations for dynamic processes

The importance of chiral organic intermediates in various industrial sectors cannot be underestimated. Lipases and their use in combination with metal catalysts is a promising and facile approach to obtain enantiomerically pure chiral intermediates like alcohols and amines. The area of lipase-mediated kinetic resolution (KR) and its dynamic counterpart (dynamic kinetic resolution, DKR) employing lipases and metal based racemization catalysts has shown extensive and stimulating advances in the recent years. The present review highlights the recent progress in this field pertaining to the development of transition metal based racemization catalysts for utilization in DKR protocols and also widening of the application for a range of chiral alcohols and amines that are employed as substrates in lipase catalyzed KR. In addition, the developments in the lipase catalyzed protocols to access other chiral intermediates such as esters, amides, aminoacids etc and their derivatives are also discussed.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Chiral pyridinyloxazolidine ligands and copper chloride complexes

Two chiral bidentate C1-symmetric 1,3-oxazolidine ligands (1 and 2) and coordination complexes with copper(II) chloride (Cu2C 14(C15H14H2O)2 (3) and [Cu2C14(C16H16N2O)2]CH 30H (4)) were synthesized and characterized by X-ray crystallographic techniques. The ligands maintain the same stereochemistry within all structures, resulting in an anti-relationship between the 2,4-substituents. Structures 3 and 4 dimerized through bridging chlorides and 3 has an extended hydrogen bonding network resulting in an infinite 1D chain.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Photochemical studies on bicyclo[2.1.1]hexyl derivatives: Chemical behavior and asymmetric induction

The photochemical behavior of bicyclo[2.1.1]hexyl derivatives was investigated by irradiation with a 450 W medium-pressure mercury lamp in acetonitrile solution. The irradiation of methyl bicyclo[2.1.1]hexane-5- carbonylbenzoate (1a) led to both Norrish type II cyclization and cleavage products with a molar ratio of 1:2.2, whereas the irradiation of methyl 5-methylbicyclo[2.1.1]hexane-5-carbonylbenzoate (1b) afforded the only Norrish/Yang photocyclization compound as the sole product. Such results were illustrated by several geometric parameters for Norrish/Yang photoreaction as phi1, phi4 and beta obtained from the crystal structures. Furthermore, asymmetric photochemical studies using ionic chiral auxiliary technique were also conducted in the solid state. Bicyclo[2.1.1] hexanyl derivatives were synthesized and their photochemical behaviour was investigated in acetonitrile solution. Copyright

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Evaluation of ligands for ketone reduction by asymmetric hydride transfer in water by multi-substrate screening

Various ligands for the ruthenium-catalyzed enantioselective reduction of ketones in water have been investigated. Multi-substrate reactions have been carried out for the comparison of various proline amides and aminoalcohol ligands. Two sets of six aromatic ketones have been selected in order to evaluate the enantiomeric excesses of all the resulting alcohols by a single chromatographic analysis. The proline amide derivative prepared from (1R,2S)-cis-aminoindanol revealed as the best ligand for most of the ketones used in the multi-substrate reductions. This ligand has been employed for the enantioselective reduction of a variety of other aromatic ketones and in all cases the enantiomeric excesses were improved compared to those obtained with phenylprolineamide used in our previous work.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Synthetic Route of 126456-43-7, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 126456-43-7, molcular formula is C9H11NO, introducing its new discovery.

Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Exocyclic C=C Bonds

An iridium-catalyzed asymmetric hydrogenation of unfunctionalized exocyclic C=C bonds was performed by using an axially flexible chiral phosphine?oxazoline ligand, providing the desired chiral 1-benzyl-2,3-dihydro-1H-indene products with up to 98 % ee (enantiomeric excess). This represents the first general hydrogenation of unfunctionalized exocyclic olefins with high selectivity reported thus far. The additive acetate ion plays an important role in the reaction’s high enantioselectivity. The chiral product can be further transformed into key intermediates required for the synthesis of an important insecticide and a drug compound.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Extended knowledge of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Epimerization of diastereomeric alpha-amino nitriles to single stereoisomers in the solid state

A diastereomeric mixture of the alpha-amino nitrile prepared by the Strecker reaction of benzaldehyde, (1S,2R)-1-aminoindan-2-ol, and cyanotrimethylsilane thermally epimerizes in the solid state to give a single diastereomer with an (S)-configuration at the alpha position to the nitrile moiety. This shows a sharp contrast to the reaction conducted in DMSO at room temperature, which gives a 1:1 mixture of (S)- and (R)-isomers. Several other alpha-amino nitriles also epimerize in the solid-state toward single diastereomers.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis