Category: 943757-71-9

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Combining cycloisomerization with trienamine catalysis: A regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles

The synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselectivity, with the regioselectivity of cycloaddition with respect to the tethering ring readily tuned through design of the cycloisomerization substrate. This work culminates in the first examples of double-stereodifferentiating trienamine catalysis, where catalyst stereocontrol dominates facial selectivity in the cycloaddition, affording azacyclic products that are specifically functionalized at every position.

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

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An asymmetric organocatalytic quadruple cascade initiated by a Friedel-Crafts-type reaction with electron-rich arenes

An organocatalytic quadruple domino reaction initiated by a Friedel-Crafts-type reaction of electron-rich arenes is described. The procedure involving up to three different Michael acceptors afforded highly functionalized cyclohexenecarbaldehydes bearing an aniline moiety, which are of great pharmaceutical and agricultural interest. This diphenylprolinol trimethylsilyl ether-catalyzed reaction also generates up to 4 contiguous stereocenters. It could be shown that various functional groups are tolerated and all products were obtained with very good diastereo- and excellent enantioselectivity. Copyright

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

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Enantioselective Organocatalytic Cascade Approach to Different Classes of Benzofused Acetals

A novel enantioselective organocatalytic strategy is presented for the synthesis of tetrahydrofurobenzofuran and methanobenzodioxepine natural product core structures. The strategy is based on a pair of divergent reaction pathways in which hydroxyarenes react with gamma-keto-alpha,beta-unsaturated aldehydes, catalyzed by a chiral secondary amine. One reaction pathway, which leads to chiral 5,5-fused acetals with two stereocenters?the tetrahydrofurobenzofuran scaffolds?proceeds in moderate yields and up to 96 % ee. The other reaction pathway provides 5,6-bridged methanobenzodioxepine scaffolds with three stereocenters in moderate to good yields and up to 95 % ee. The reaction is remarkable as it can proceed with catalyst loadings as low as 0.25 mol %, providing one of the highest known turnover numbers in iminium ion catalysis. Furthermore, the hemiacetal tetrahydrofurobenzofuran can undergo functionalizations including reduction, oxidation, and allylation. Finally, the effects involved in the substrate control for the divergent pathways, based on both experimental and computational studies, have been investigated. A model involving steric, electronic and stereoelectronic interactions is discussed to rationalize the observed selectivities.

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

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A 3 – benzyloxymethyl – 4 – aryl – 5 – nitro – 1 – formyl cyclohexene preparation method (by machine translation)

The invention relates to a 3 – benzyloxymethyl – 4 – aryl – 5 – nitro – 1 – formyl cyclohexene preparation method, the 3 – benzyloxymethyl – 4 – aryl – 5 – nitro – 1 – formyl cyclohexene structure as shown in formula I: In the formula R is a substituted, disubstituted, trisubstituted and four substituted halogen, nitro, amino, 1 – 10 carbon alkyl or 1 – 10 alkoxy; preparation method comprises the following: the 3 – benzyloxy propionaldehyde, (E)- (2 – nitroethylene) aromatic compound with a secondary amine and solvent mixed, for 0 – 25 C reaction 1 – 24 hours later, by washing, extraction, separation, to obtain 3 – benzyloxymethyl – 4 – aryl – 5 – nitro – 1 – formyl cyclohexene; The present invention provides synthetic method is simple in operation, mild reaction conditions, does not need to be water-free, oxygen-free processing, does not need to be low-temperature refrigeration. Yield of the object product, the resulting of the target product as a single isomer, in optical pure catalyst catalyzes the reaction of the enantioselectivity is greater than 99% ee. (by machine translation)

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. category: catalyst-ligand, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 943757-71-9, in my other articles.

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

Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent£¬ Quality Control of: (R)-2-(Diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine, Which mentioned a new discovery about 943757-71-9

Two Reaction Mechanisms via Iminium Ion Intermediates: The Different Reactivities of Diphenylprolinol Silyl Ether and Trifluoromethyl-Substituted Diarylprolinol Silyl Ether

The reactions of alpha,beta-unsaturated aldehydes with cyclopentadiene in the presence of diarylprolinol silyl ethers as catalyst proceed via iminium cations as intermediates, and can be divided into two types; one involving a Michael-type reaction (type A) and one involving a cycloaddition (type B). Diphenylprolinol silyl ethers and trifluoromethyl-substituted diarylprolinol silyl ethers, which are widely used proline-type organocatalysts, have been investigated in this study. As the LUMO of the iminium ion derived from trifluoromethyl-substituted diarylprolinol silyl ether is lower in energy than that derived from diphenylprolinol silyl ether, as supported by ab initio calculations, the trifluoromethyl-substituted catalyst is more reactive in a type B reaction. The iminium ion from an alpha,beta-unsaturated aldehyde is generated more quickly with diphenylprolinol silyl ether than with the trifluoromethyl-substituted diarylprolinol silyl ether. When the generation of the iminium ion is the rate-determining step, the diphenylprolinol silyl ether catalyst is the more reactive. Because acid accelerates the generation of iminium ions and reduces the generation of anionic nucleophiles in the Michael-type reaction (type A), it is necessary to select the appropriate acid for specific reactions. In general, diphenylprolinol silyl ether is a superior catalyst for type A reactions, whereas the trifluoromethyl-substituted diarylprolinol silyl ether catalyst is preferred for type B reactions.

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

In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 943757-71-9, name is (R)-2-(Diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine, introducing its new discovery. COA of Formula: C20H27NOSi

P-nitrophenyl ethylthioester in enantioselective organocatalytic Michael additions: Different behaviour of beta-aryl and beta-alkyl enals

Although several nucleophiles derived from arylacetic acids have been described in catalysis via iminium activation, none have presented good enantioselectivity and reactivity with both beta-alkyl and beta-aryl enals. This study on the Michael addition of p-nitrophenylacetic thioesters suggests that this behavior is due to the different reactivity and distinct tendency to reversibility exhibited by these types of enal. Independent optimization of the conditions for beta-alkyl and beta-aryl enals provide good yields and enantioselectivities with both substrates, affording Michael adducts that are versatile building blocks for the preparation of an interesting variety of arylacetic acid derivatives. S-Ethyl 4-nitrophenylthioacetate presents excellent reactivity and enantioselectivity in organocatalytic asymmetric Michael reactions with both aromatic and aliphatic enals under different conditions. The corresponding adducts have proven to be versatile intermediates. Copyright

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 943757-71-9 is helpful to your research. COA of Formula: C20H27NOSi

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

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, 943757-71-9, molcular formula is C20H27NOSi, introducing its new discovery. Computed Properties of C20H27NOSi

alpha-Oxo-beta-butyrolactam, N -containing pronucleophile in organocatalytic one-pot assembly of butyrolactam-fused indoloquinolizidines

The ambident reactivity of alpha-oxo-beta-butyrolactam has been explored in an organocatalytic one-pot Michael/Pictet-Spengler sequence. The synthetically interesting and medicinally important pentacyclic butyrolactam-fused indoloquinolizidines can be efficiently constructed in a highly stereocontrolled manner. Importantly, the chemistry described herein provides a general catalytic method for the enantioselective synthesis of butyrolactam-incorporated chemical entities.

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

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, 943757-71-9, molcular formula is C20H27NOSi, introducing its new discovery. Safety of (R)-2-(Diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine

alpha-Oxo-beta-butyrolactam, N -containing pronucleophile in organocatalytic one-pot assembly of butyrolactam-fused indoloquinolizidines

The ambident reactivity of alpha-oxo-beta-butyrolactam has been explored in an organocatalytic one-pot Michael/Pictet-Spengler sequence. The synthetically interesting and medicinally important pentacyclic butyrolactam-fused indoloquinolizidines can be efficiently constructed in a highly stereocontrolled manner. Importantly, the chemistry described herein provides a general catalytic method for the enantioselective synthesis of butyrolactam-incorporated chemical entities.

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

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Dienamine and friedel-crafts one-pot synthesis, and antitumor evaluation of diheteroarylalkanals

An asymmetric synthesis of diheteroarylalkanals through one-pot dienamine and Friedel-Crafts reaction is presented. The reaction tolerates a large variety of substituents at different positions of the starting aldehyde and also in the indole nucleophile, and a range of diheterocyclic alkanals can be achieved. Furthermore, we have studied the antiproliferative activity of these new compounds in representative cancer tumor cell lines. All in one: An asymmetric synthesis of diheteroarylalkanals through a one-pot dienamine and Friedel-Crafts reaction is presented (see scheme). The reaction tolerates a large variety of substituents at different positions of the starting aldehyde, and the use of nucleophiles and different diheterocyclic alkanals can also be achieved. The antiproliferative activity of these new compounds in different cancer tumor cell lines has also been investigated and it was found that, with the appropriate substitution, the compounds are as cytotoxic as Cisplatin.

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

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Scalable Synthesis of (-)-Rasfonin Enabled by a Convergent Enantioselective alpha-Hydroxymethylation Strategy

A scalable synthesis of the potent antitumor agent, (-)-rasfonin, has been achieved. The synthetic strategy features a highly convergent approach based on a single protocol construction of both major fragments via catalytic enantioselective alpha-hydroxymethylation of simple aliphatic aldehydes. The route described has been successful in the generation of gram quantities of the natural product and serves as the first synthetic strategy to provide sufficient material to continue studies related to its mechanism of action and potential as a cancer therapeutic.

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