1044499-41-3

Upstream product

• 1044499-32-2 C₁₅H₁₁F₃N₂O₄S 
• 121998-76-3 2-phenyl-2,3-dihydro-4(1H)-quinazolinone 
• 100-52-7 benzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 88-05-1 2,4,6-trimethylaniline 
• 118847-62-4 N,N-dimethyl-N'-(phenylmethylene)sulfamide 
• 831225-94-6 N-phenylmethylidene-2,4,6-triisopropylbenzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 95-55-6 2-amino-phenol 
• 62-53-3 aniline 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 538-51-2 benzylidene phenylamine 
• 98837-46-8 P,P-diphenyl-N-(phenylmethylene)phosphinic amide 
• 14674-32-9 N-Benzyliden-3-nitrobenzolsulfonamid 

Relevant academic research and scientific papers

Practical catalytic enantioselective synthesis of 2,3-dihydroquin-azolinones by chiral br?nsted acid catalysis

Herein, we report on the highly efficient and practical synthesis of 2,3-dihydroquinazolinones directly from diverse aldehydes with excellent yields and enantioselectivity. Particularly, this protocol affords better enantiocontrol for aliphatic aldehydes

Homochiral Dodecanuclear Lanthanide "cage in Cage" for Enantioselective Separation

It is extremely difficult to anticipate the structure and the stereochemistry of a complex, particularly when the ligand is flexible and the metal node adopts diverse coordination numbers. When trivalent lanthanides (LnIII) and enantiopure amino acid ligands are utilized as building blocks, self-assembly sometimes yields rare chiral polynuclear structures. In this study, an enantiopure carboxyl-functionalized amino acid-based ligand with C3 symmetry reacts with lanthanum cations to give a homochiral porous coordination cage, (Δ/λ)12-PCC-57. The dodecanuclear lanthanide cage has an unprecedented octahedral "cage-in-cage"framework. During the self-assembly, the chirality is transferred from the enantiopure ligand and fixed by the binuclear lanthanide cluster to give 12 metal centers that have either Δor λ homochiral stereochemistry. The cage exhibits excellent enantioselective separation of racemic alcohols, 2,3-dihydroquinazolinones, and multiple commercially available drugs. This finding exhibits a rare example of a multinuclear lanthanide complex with a dual-walled topology and homochirality. The highly ordered self-assembly and self-sorting of flexible amino acids and lanthanides shed light on the chiral transformation between different complicated artificial systems that mimic natural enzymes.

Confinement-Driven Enantioselectivity in 3D Porous Chiral Covalent Organic Frameworks

3D covalent organic frameworks (COFs) with well-defined porous channels are shown to be capable of inducing chiral molecular catalysts from non-enantioselective to highly enantioselective in catalyzing organic transformations. By condensations of a tetrahedral tetraamine and two linear dialdehydes derived from enantiopure 1,1′-binaphthol (BINOL), two chiral 3D COFs with a 9-fold or 11-fold interpenetrated diamondoid framework are prepared. Enhanced Br?nsted acidity was observed for the chiral BINOL units that are uniformly distributed within the tubular channels compared to the non-immobilized acids. This facilitates the Br?nsted acid catalysis of cyclocondensation of aldehydes and anthranilamides to produce 2,3-dihydroquinazolinones. DFT calculations show the COF catalyst provides preferential secondary interactions between the substrate and framework to induce enantioselectivities that are not achievable in homogeneous systems.

Enantioselective PCCP Br?nsted acid-catalyzed aminalization of aldehydes

Here we present an enantioselective aminalization of aldehydes catalyzed by Br?nsted acids based on pentacarboxycyclopentadienes (PCCPs). The cyclization reaction using readily available anthranilamides as building blocks provides access to valuable 2,3-dihydroquinazolinones containing one stereogenic carbon center with good enantioselectivity (ee up to 80%) and excellent yields (up to 97%).

Adamantyl-BINOL as platform for chiral porous polymer aromatic frameworks. Multiple applications as recyclable catalysts

Herein, we report the synthesis of adamantyl-BINOL-based chiral porous aromatic polymers (Ad-BINOL-PAFs) for heterogeneous catalysis. Ad-BINOL-OH-PAF (365 m2·g?1 SABET) was built through the covalent bonds among of 4,4′-dibromo-O-ethyl-protected adamantyl-BINOL with 1,3,5-Triphenylbenzene-4′,4″,4′″-triboronic acid and in the presence of [Ti(OiPr)4] results an effective recyclable catalyst in the asymmetric addition of diethylzinc to aromatic aldehydes (ee up to 88%). The corresponding heterogenized phosphoric acid (Ad-BINOL-PO2H-PAF) was applied as heterogeneous recyclable organocatalyst for the cascade condensation/amine addition of anthranilamide with aldehydes and transfer hydrogenation reactions obtaining high yields but low enantioselectivity. On the other hand, heterogeneous phosphoric acid (Ad-BINOLs-PO2H-PAF) was also used as effective phosphate ligands for synthesis of rhodium(II) complexes which were effective catalysts in cyclopropanation of styrene affording chiral cyclopropanes in good yield and high diastereoselectivity (>99%) and moderate enantioselectivity (ee 50%).

Chiral Phosphoric Acids in Metal–Organic Frameworks with Enhanced Acidity and Tunable Catalytic Selectivity

Chiral phosphoric acids are incorporated into indium-based metal–organic frameworks (In-MOFs) by sterically preventing them from coordination. This concept leads to the synthesis of three chiral porous 3D In-MOFs with different network topologies constructed from three enantiopure 1,1′-biphenol-phosphoric acid derived tetracarboxylate linkers. More importantly, all the uncoordinated phosphoric acid groups are periodically aligned within the channels and display significantly enhanced acidity compared to the non-immobilized acids. This facilitates the Br?nsted acid catalysis of asymmetric condensation/amine addition and imine reduction. The enantioselectivities can be tuned (up to '99 % ee) by varying the substituents to achieve a nearly linear correlation with the concentrations of steric bulky groups in the MOFs. DFT calculations suggest that the framework provides a chiral confined microenvironment that dictates both selectivity and reactivity of chiral MOFs.

Boosting Enantioselectivity of Chiral Organocatalysts with Ultrathin Two-Dimensional Metal-Organic Framework Nanosheets

The development of methodologies for inducing and tailoring enantioselectivities of catalysts is an important issue in asymmetric catalysis. In this work, we demonstrate for the first time that chiral molecular catalysts can be boosted from completely nonselective to highly enantioselective when installed in nanostructured metal-organic frameworks (MOFs). Exfoliation of layered crystals is one of the most direct synthetic routes to unltrathin nanosheets, but its use in MOFs is limited by the availability of layered MOFs. We illustrate that layered MOFs can be designed using ligand-capped metal clusters and angular organic linkers. This leads to the synthesis of two three-dimensional (3D) layered porous MOFs from Zn4-p-tert-butylsulfonyl calix[4]arene and chiral angular 1,1′-binaphthol/-biphenol dicarboxylic acids, which can be ultrasonic exfoliated into one- and two-layer nanosheets. The obtained MOF materials are efficient catalysts for asymmetric cascade condensation and cyclization of 2-aminobenzamide and aldehydes to produce 2,3-dihyroquinazolinones. While both binaphthol and biphenol display no enantioselectivity, restriction of their freedom in the MOFs leads to 56-90% and 46-72% ee, respectively, which are increased to 72-94% and 64-82% ee after exposure to external surfaces of the flexible nanosheets. Moreover, the MOF crystals and nanosheets exhibit highly sensitive fluorescent enhancement in the presence of chiral amino alcohols with enantioselectivity factors being, respectively, increased up to 1.4 and 2.3 times of the values of the diols, allowing them to be utilized in chiral sensing. Therefore, the observed enantioselectivities increase in the order organocatalyst MOF crystals MOF nanosheets in both catalysis and sensing. This work not only provides a strategy to make 3D layered MOFs and their untrathin nanosheets but also paves the way to utilize nanostructured MOFs to manipulate enantioselectivities of molecular catalysts.

OPTICALLY ACTIVE BINAPHTHYL COMPOUND

PROBLEM TO BE SOLVED: To provide an optically active binaphthyl compound useful as a catalyst for asymmetric synthesis by conversion into a dibasic acid having a functional group different in acidity, which is a new compound having a chemical structure different from a binaphthyl-based compound previously presented. SOLUTION: There is provided an optically active binaphthyl compound represented by the formula (1). [R1 represents a substituted/unsubstituted linear, branched or cyclic alkyl group having 1 to 12 carbon atoms, an aryl group or an aromatic heterocyclic group; R2 and R3 each independently represents H, a substituted/unsubstituted linear, branched or cyclic alkyl group having 1 to 12 carbon atoms, an aryl group or an aromatic heterocyclic group; and E represents O or S.] SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Highly enantioselective synthesis of dihydroquinazolinones through Sc(OTf)3-catalyzed intramolecular amidation of imines

A Sc(OTf)3-catalyzed intramolecular amidation of imines with a novel fluorous bis(oxazolines) as ligand is presented. The corresponding chiral dihydroquinazolinones were obtained in 76-94% yield with enantioselectivities up to 98%. The fluorous ligand can be easily recovered and reused at least three times without significant loss of enantioselectivity.

Investigation of the enantioselective synthesis of 2,3- Dihydroquinazolinones Using Sc(III)- Inda -pybox

Derivatives of 2,3-dihydroquinazolinones (2,3-DHQZs) are prized for their prevalent pharmaceutical applications. Although there are potential applications, methods available for the enantioselective synthesis of these valuable compounds are scarce, since the chiral aminal center is prone to racemization. We have overcome the difficulties in the catalytic enantioselective synthesis of 2,3-DHQZs using Sc(III)-inda-pybox as a catalyst, in a process with a broad substrate scope. Georg Thieme Verlag Stuttgart. New York.