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A highly potential analogue of Jacobsen catalyst with in-built phase transfer capability in enantioselective epoxidation of nonfunctionalized alkenes

A new analogue of Jacobsen MnIII SALEN epoxidation catalysts having in-built phase transfer capability by means of introducing tertiary amino alkyl groups at the 5,5?-position of the Salen ligand were used as catalysts for the liquid-phase enantioselective epoxidation of 2,2-dimethyl-6-cyano chromene, indene, and styrene in the presence of O-coordinating axial bases with NaOCl as an oxidant under biphasic reaction conditions. Excellent conversions were obtained with catalyst loading in the range 0.4-2.0 mol% in all alkenes, but high chiral induction (EEs > 99%) was obtained only in the case of 2,2-dimethyl-6-cyano chromene. The enhanced activity of these complexes is attributed to the presence of t-alkyl amines in the Salen ligand, imparting in-built phase transfer capability to the catalyst.

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Chiral Catalysts,
Chiral catalysts – SlideShare

 

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Electron delocalization in a rigid cofacial naphthalene-1,8:4,5- bis(dicarboximide) dimer

Investigating through-space electronic communication between discrete cofacially oriented aromatic pi-systems is fundamental to understanding assemblies as diverse as double-stranded DNA, organic photovoltaics and thin-film transistors. A detailed understanding of the electronic interactions involved rests on making the appropriate molecular compounds with rigid covalent scaffolds and pi-pi distances in the range of ca. 3.5 A. Reported herein is an enantiomeric pair of doubly-bridged naphthalene-1,8:4,5- bis(dicarboximide) (NDI) cyclophanes and the characterization of four of their electronic states, namely 1) the ground state, 2) the exciton coupled singlet excited state, 3) the radical anion with strong through-space interactions between the redox-active NDI molecules, and 4) the diamagnetic diradical dianion using UV/Vis/NIR, EPR and ENDOR spectroscopies in addition to X-ray crystallography. Despite the unfavorable Coulombic repulsion, the singlet diradical dianion dimer of NDI shows a more pronounced intramolecular pi-pi stacking interaction when compared with its neutral analog. Two are better than one: A doubly-bridged naphthalene diimide (NDI) cyclophane has been synthesized. It shows efficient pi-orbital overlap between two rigid cofacial NDI units. The resulting through-space electronic delocalization in the neutral as well as reduced states induces emergent photophysical, electrochemical, and magnetic properties both in solution and in the solid phase.

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Chiral Catalysts,
Chiral catalysts – SlideShare

 

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A highly potential analogue of Jacobsen catalyst with in-built phase transfer capability in enantioselective epoxidation of nonfunctionalized alkenes

A new analogue of Jacobsen MnIII SALEN epoxidation catalysts having in-built phase transfer capability by means of introducing tertiary amino alkyl groups at the 5,5?-position of the Salen ligand were used as catalysts for the liquid-phase enantioselective epoxidation of 2,2-dimethyl-6-cyano chromene, indene, and styrene in the presence of O-coordinating axial bases with NaOCl as an oxidant under biphasic reaction conditions. Excellent conversions were obtained with catalyst loading in the range 0.4-2.0 mol% in all alkenes, but high chiral induction (EEs > 99%) was obtained only in the case of 2,2-dimethyl-6-cyano chromene. The enhanced activity of these complexes is attributed to the presence of t-alkyl amines in the Salen ligand, imparting in-built phase transfer capability to the catalyst.

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Reference£º
Chiral Catalysts,
Chiral catalysts – SlideShare

 

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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.21436-03-3. In my other articles, you can also check out more blogs about 21436-03-3

21436-03-3, Name is (1S,2S)-Cyclohexane-1,2-diamine, molecular formula is C6H14N2, belongs to chiral-catalyst compound, is a common compound. In a patnet, once mentioned the new application about 21436-03-3, 21436-03-3

Electron delocalization in a rigid cofacial naphthalene-1,8:4,5- bis(dicarboximide) dimer

Investigating through-space electronic communication between discrete cofacially oriented aromatic pi-systems is fundamental to understanding assemblies as diverse as double-stranded DNA, organic photovoltaics and thin-film transistors. A detailed understanding of the electronic interactions involved rests on making the appropriate molecular compounds with rigid covalent scaffolds and pi-pi distances in the range of ca. 3.5 A. Reported herein is an enantiomeric pair of doubly-bridged naphthalene-1,8:4,5- bis(dicarboximide) (NDI) cyclophanes and the characterization of four of their electronic states, namely 1) the ground state, 2) the exciton coupled singlet excited state, 3) the radical anion with strong through-space interactions between the redox-active NDI molecules, and 4) the diamagnetic diradical dianion using UV/Vis/NIR, EPR and ENDOR spectroscopies in addition to X-ray crystallography. Despite the unfavorable Coulombic repulsion, the singlet diradical dianion dimer of NDI shows a more pronounced intramolecular pi-pi stacking interaction when compared with its neutral analog. Two are better than one: A doubly-bridged naphthalene diimide (NDI) cyclophane has been synthesized. It shows efficient pi-orbital overlap between two rigid cofacial NDI units. The resulting through-space electronic delocalization in the neutral as well as reduced states induces emergent photophysical, electrochemical, and magnetic properties both in solution and in the solid phase.

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Chiral Catalysts,
Chiral catalysts – SlideShare

 

Some scientific research about (1S,2S)-Cyclohexane-1,2-diamine

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Highly enantio- and regioselective allylic alkylations catalyzed by chiral [bis(dihydrooxazole)]molybdenum complexes

A series of chiral C2-symmetric bis[dihydrooxazoles] with a trans-1,2-diaminocyclohexane backbone was synthesized. In view of the promising results obtained by Trost et al. with related bis[pyridine] ligands, we tested these new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates. Enantiomer excesses of up to 98% and branched/linear ratios of up to 11:1 were obtained with (E)-3-(alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branched/linear ratio of > 20:1 and an ee of 98%. Crystal structures of the free ligand 7a and of its tricarbonylmolybdenum(0) complex 28 are reported.

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Chiral Catalysts,
Chiral catalysts – SlideShare

 

Properties and Exciting Facts About (1S,2S)-Cyclohexane-1,2-diamine

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Pantothenic acid derivatives

Compounds represented by general formula (I) below STR1 wherein R1 and R2, which are the same or different, each represent a hydrogen atom or a protective group for a hydroxyl group; R3 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5 ?C25 -aliphatic hydrocarbon group which may be substituted with an aromatic group, or a group of formula STR2 where R4 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5 ?C25 -aliphatic hydrocarbon group which may be substituted with an aromatic group, and R5 represents a hydrogen atom, or a saturated or unsaturated, linear, branched or cyclic, monovalent hydrovarbon group which may be substituted with an aromatic group; Q represents (a) a group of formula –X1 –A–Y1 –, where A represents a saturated or unsaturated, linear, branched or cyclic divalent C2 ?C16 -aliphatic hydrocarbon group which may be substituted with an aromativ group, a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group; one of X1 and Y1 represents STR3 and the other represents –O–, –S– or STR4 in which R6 and R7 each represent a hydrogen atom or a lower alkyl group; (b) a group of formula –X2 –(CH2)l –Y2 –, where one of X2 and Y2 represents a group of formula STR5 and the other represents –O–, –S– or STR6 in which STR7 represents a 4?7-membered, divalent nitrogen-containing aromatic heterocyclic group, and R6 has the same meaning as defined above, and l is 0, 1 or 2; or (c) a group of formula STR8 where m is 2 or 3; n is an integer of from 1 to 4. The compounds have excellent inhibitory activity against acyl Co A-cholesterol-acyltransferase.

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Chiral Catalysts,
Chiral catalysts – SlideShare

 

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Asymmetric Baeyer-Villiger reaction with hydrogen peroxide catalyzed by a novel planar-chiral bisflavin

The chiral organocatalyst bisflavin 1 catalyzes the asymmetric Baeyer-Villiger reaction of cyclobutanones with H2O2 (see scheme). The corresponding lactones are obtained with up to 74% ee.

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Chiral Catalysts,
Chiral catalysts – SlideShare

 

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C(sp2)?H Hydrogen-Bond Donor Groups in Chiral Small-Molecule Organocatalysts

Asymmetric catalysis of chemical transformations by chiral small organic molecules has become an important approach in organic synthesis. Attractive noncovalent interactions such as N(O)?H hydrogen-bonding, pi-stacking, and cation-pi interactions have been exploited as the primary and/or secondary function(s) of the catalysts, but C(sp2)?H hydrogen-bonding interactions have been underutilized in this context. This Minireview showcases selected organocatalysts in which C(sp2)?H hydrogen-bonding interactions are invoked in their mechanism of catalysis, examples of which can be inspirational for the development of new catalysts.

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Chiral Catalysts,
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Chiral primary amine-polyoxometalate acid hybrids as asymmetric recoverable iminium-based catalysts

A new strategy for the immobilization of iminium organocatalysts through, the acid-base assembly of multidentate chiral primary amines and solid polyacids is presented, A suitable structurally distinctive C2-symmetric chiral primary amine (CPA) was identified in this study and the optimal CPA-POM hybrid obtained catalyzed the Diels-Alder cycloaddition of a-substituted acroleins in high yields and fair-to-high selectivity under aqueous conditions. The primary amine in the metal-organic-framework (MOF)-like catalyst acted as the catalytic center as well as multidentate basic centers, whereas phosphotungstic acid played dual roles as both catalyst anchors and modulators of the activity and stereoselectivity, Furthermore, the MOF-like catalyst showed both high reactivity and physical stability and thus could be recycled and reused six. times with only a small loss of activity and selectivity.

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Chiral Catalysts,
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Discovery of (1S,2S)-Cyclohexane-1,2-diamine

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Time Dependent Structural Evolution of Porous Organic Cage CC3

Herein we followed the structural evolution of a prototypical type of porous organic cage, CC3, as a function of synthesis time. Three distinctive crystal formation stages were identified: at short synthesis times, a rapid crystal growth stage in which amorphous agglomerates transformed into larger irregular particles was observed. At intermediate synthesis times, a decrease in crystal size over time was observed presumably due to crystal fragmentation, redissolution, and/or homogeneous nucleation. Finally, at longer synthesis times, a regrowth process was observed in which particles coalesced through Ostwald ripening leading to a continuous increase in crystal size. Molecular simulation studies, based on the construction of in silico CC3 models and simulation of XRD patterns and nitrogen isotherms, confirm the samples at different synthesis times to be a mixture of CC3alpha and CC3-amorphous phases. The CC3alpha phase is found to contract at different synthesis times, and the amorphous phase is found to essentially disappear at the longest synthesis time. Nitrogen and carbon dioxide adsorption properties of these CC3 phases were evaluated, and were highly dependent on synthesis time.

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Chiral Catalysts,
Chiral catalysts – SlideShare