Extracurricular laboratory:new discovery of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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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
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

Extracurricular laboratory:new discovery of 126456-43-7

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Halogen-bonding interaction stabilizing cluster-type diastereomeric salt crystals

O-Ethyl 4-chlorophenylphosphonothioic acid (1) was newly synthesized and applied as a chiral selector for the enantioseparation of racemic l-(4-halophenyl)ethylamines (halo = F, Cl, Br, I; 2a-d) through diastereomeric salt formation. The phosphonothioic acid 1 showed an excellent chirality-recognition ability for the fluorinated and iodinated amines 2a and 2d with the dramatic switch of the absolute configuration of the enantio-enriched isomers in the deposited salts from R for the amine 2a to S for the amine 2d. The X-ray crystallographic analyses of the four pairs of diastereomeric salts revealed that halogen-bonding interaction in the salt crystals plays a very important role for the switch.

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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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Divergent Synthesis of Chiral Covalent Organic Frameworks

Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functionality, in a divergent manner, into covalent organic frameworks (COFs). This modular protocol includes two stages of covalent assembly, through which functional COFs can be constructed by a three-step transformation of a key platform molecule, such as 4,7-dibromo-2-chloro-1H-benzo[d]imidazole (DBCBI). Constructed herein are four types of chiral COFs (CCOFs) from DBCBI by nucleophilic substitution, Suzuki coupling, and imine formation. The unique array of eight isoframework CCOFs allowed investigation of their catalytic performance and structure?activity relationship in an asymmetric amination reaction.

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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

A new application about 2,4-Dimethylpyridine

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STEREO- AND REGIO-SELECTIVE ALDOL-TYPE REACTIONS OF ALKYLPYRIDINES WITH BENZALDEHYDE

Stereo- and regio-selectivity in the reaction of alkylpyridines with benzaldehyde were studied.Erythro-selectivity could be obtained in the reaction of 2-alkylpyridine with benzaldehyde in the presence of dialkylboryl triflate and triethylamine.Substitution at the 2- or 4-position of 2,4-lutidine could be controlled by the combination of dialkylboryl triflate and an aliphatic tertiary amine.The steric effect had an important role in the reaction of 4-picoline and lepidine.

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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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Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram

The enantioselective synthesis of endothelin-A antagonist ABT-546 has been accomplished via the discovery and development of a highly selective catalytic asymmetric conjugate addition of ketoesters to nitroolefins. Employing just 4 mol % bis(oxazoline)-Mg(OTf)2 complex with an amine cocatalyst, we obtained the product nitroketone with 88% selectivity at the aryl-bearing stereocenter and in good yield on scales ranging to 13 mol. The effects of ligand structure, metal salt, and solvent on the reaction are described. Particularly important to the reaction is the water content. While water is necessary during the generation of the catalyst, the water must be then removed to maximize stereoselectivity and reactivity. The reaction has been extended to other dicarbonyl substrates, and a variety of substitution patterns are tolerated on the nitroolefin partner. The reaction has also been employed in the synthesis of the antidepressant rolipram. Investigations relating to the mechanism of the reaction are also described.

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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

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

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Photochemical studies on 5-methylbicyclo[1.1.1]pentane derivatives: P-orbital overlap controlled enantioselectivity

The first example of the p-orbital overlap controlled enantioselectivity of Norrish type II photocyclization reaction was described. Irradiation of 5-methyl bicyclo[1.1.1]pentanyl ketone with UV in the solid state as well as in the acetonitrile solution afforded the Norrish/Yang photocyclization compound as the sole product. Solid-state asymmetric photochemical studies using ionic chiral auxiliary technique led to the enantioselectivity as high as 60%. The results were rationalized by X-ray single crystal structure. 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

The Absolute Best Science Experiment for 108-47-4

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Facile preparation of CF3-substituted carbinols with an azine donor and subsequent kinetic resolution through stereoselective Si-O coupling

A number of CF3-substituted carbinols decorated with an azine donor are efficiently prepared from fluoral and kinetically resolved in a reagent-controlled, Cu-H-catalysed Si-O coupling with a chiral silane. Selectivity factors are high, indicating a larger steric effect than CH 3 or C6H5 groups.

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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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Related Products of 108-47-4, 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. 108-47-4, Name is 2,4-Dimethylpyridine, molecular formula is C7H9N. In a Article£¬once mentioned of 108-47-4

Crystal Structures of Three Adducts of Zinc Azide with Dimethylpyridines

Three adducts of zinc azide with 2,4-/3,4- and 3,5-dimethylpyridine (DMP), respectively, were prepared and the crystal structures determined by single crystal X-ray diffraction methods.The three compounds crystallize in the monoclinic space group P21/c with Z = 4: Zn(N3)2*2,4-DMP at 300(2) K: a = 1098.6(4), b = 1600.2(6), c = 608.8(3) pm, beta = 102.47(3) deg; R = 0.071 (RW = 0.056).Zn(N3)2*3,4-DMP at 103(3) K: a = 1102.1(3), b = 1.649.0(4), c = 611.8(1) pm, beta = 104.54(2) deg; R = 0.055 (RW = 0.051).Zn(N3)2*3,5-DMP at 97(3) K: a = 602.1(2), b = 2037.9(7), c = 853.8(3) pm, beta = 90.77(3) deg; R = 0.069 (RW = 0.055).The molecular geometry is similar for the three adducts, but the packing of the DMP-molecules is different.The zinc atoms are surrounded by five nitrogen atoms, four belonging to the azide groups and one to the DMP-adduct.The trigonal bipyramidal shaped ZnN5-polyhedra share common edges to form chains.Keywords.Azide; Crystal structure; Dimethylpyridine; Zinc.

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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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Iridium-catalyzed Decarbonylative Coupling of Acyl Fluorides with Arenes and Heteroarenes via C-H Activation

The first method for decarbonylative direct arylation using acyl fluorides is reported. This reaction proceeds, only when acyl fluorides are used, and other acyl halides cannot be used. The reaction can be applied to the direct arylation of a variety of substrates, including xylene, quinoline, and benzothiophene.

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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

The important role of 2,4-Dimethylpyridine

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Highly efficient synthesis of o-(2,4-dinitrophenyl)hydroxylamine. Application to the synthesis of substituted N-benzoyliminopyridinium ylides

An efficient two-step synthesis of O-(2,4-dinitrophenyl)hydroxylamine is described along with a comparison of its aminating efficiency with O-mesitylenesulfonylhydroxylamine (MSH). It was used in an expedient N-amination/benzoylation procedure involving various substituted pyridines, leading to polysubstituted N-benzoyliminopyridinium ylides, and the scope of its amination power was studied.

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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