Category: 79815-20-6

Georgieva, Miglena K.; Duarte, Filipe J. S.; Santos, A. Gil published an article in 2016, the title of the article was Directed electrostatic activation in enantioselective organocatalytic cyclopropanation reactions: a computational study.COA of Formula: C9H9NO2 And the article contains the following content:

Cyclopropane rings are versatile building blocks in organic chem. Their synthesis, by the reaction of sulfur ylides with α,β-unsaturated carbonyl compounds, has recently aroused renewed interest after the discovery of efficient catalysis by using (S)-indoline-2-carboxylic acid. In order to rationalize the behavior of this catalyst, MacMillan proposed a directed electrostatic activation (DEA) mechanism, in which the neg. carboxylate group interacts with the pos. thionium moiety, thus reducing the activation energy and increasing the reaction rate. More recently, Mayr refuted some of MacMillan conclusions, but accepted the DEA mechanism as a justification for the exptl. high reaction rates. In contrast, our results indicate that the selectivity obtained in the process seems to result from several strong hydrogen bond interactions between the two reacting species, while no strong evidence for a DEA mechanism was found. We also concluded that the hydrogen bonds don’t improve the reaction rate by lowering the activation energy of the rate-determining step, but can do it by promoting efficient reaction trajectories due to long-range complexation of the reagents. Finally, our results confirm that the cyclopropanation reaction occurs by a two-step mechanism, and that the overall enantioselectivity depends on the relative energies of the two steps, averaged by the relative populations of the iminium intermediates that are initially formed in the reaction. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).COA of Formula: C9H9NO2

The Article related to enantioselective cyclopropanation catalyst mechanism kinetics activation energy, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.COA of Formula: C9H9NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On October 31, 2009, Luo, Ren-Shi; Weng, Jiang; Ai, Hui-Bing; Lu, Gui; Chan, Albert S. C. published an article.Application In Synthesis of H-Idc-OH The title of the article was Highly efficient asymmetric Michael reaction of aldehydes to nitroalkenes with diphenylperhydroindolinol silyl ethers as organocatalysts. And the article contained the following:

New dihydroindole and perhydroindole derivatives were synthesized in good yields and evaluated as chiral catalysts in the asym. Michael reaction of aldehydes to nitroalkenes. (2S,3aS,7aS)-Diphenylperhydroindolinol silyl ether facilitated the reaction of a wide range of aldehyde and nitroalkene substrates, providing Michael adducts in nearly optically pure form (99% ee), good yields and high diastereoselectivities (syn/anti up to 99:1). These results show that perhydroindole derivatives can be highly efficient organocatalysts for the asym. Michael reaction, exhibiting comparable or even better enantioselectivities than proline derivatives The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Application In Synthesis of H-Idc-OH

The Article related to michael stereoselective aldehyde nitroalkene silyloxydiphenylmethylindole catalyst, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Aldehydes and Derivatives, Including Sulfur Analogs and other aspects.Application In Synthesis of H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On November 30, 2008, Jainta, Manuel; Nieger, Martin; Brase, Stefan published an article.Application In Synthesis of H-Idc-OH The title of the article was Microwave-assisted stereoselective one-pot synthesis of symmetrical and unsymmetrical 2,5-diketopiperazines from unprotected amino acids. And the article contained the following:

The facile condensation of unprotected amino acids by phosphite-promoted one-step coupling reaction is a highly efficient synthesis to generate stereoselective and optically pure sym. and unsym. functionalized diketopiperazines. The use of microwaves enhanced by small amounts of ionic liquid is accompanied by significant improvement in reaction times and yields. Simple filtration through a pad of silica provides the pure compounds in very good to excellent yields. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Application In Synthesis of H-Idc-OH

The Article related to diketopiperazine derivative preparation, amino acid cyclization, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Application In Synthesis of H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Das, Krishna Kanta; Ghosh, Asim Kumar; Hajra, Alakananda published an article in 2022, the title of the article was Late-stage ortho-C-H alkenylation of 2-arylindazoles in aqueous medium by Manganese(I)-catalysis.Synthetic Route of 79815-20-6 And the article contains the following content:

Earth-abundant and water-tolerant manganese(I) catalyzed alkenylation of 2-arylindazoles I (R = H, F, Cl; R1 = H, 4-Me, 3-Cl, etc.) with alkyl and aryl alkynes R2CCR3 (R2 = H, Ph, Me; R3 = hexyl, Ph, thiophen-3-yl, etc.) through C-H bond activation is described with a unique level of E-selectivity. The reaction proceeds through the control of C3 nucleophilicity of 2-aryl indazoles. This method is applied to the late-stage functionalization of complex mols. including ethinylestradiol, norethisterone, and N-protected amino acid derivatives, e.g., prop-2-yn-1-yl (tert-butoxycarbonyl)-L-phenylalaninate. The kinetic isotope studies suggest that the C-H bond activation step may not be the rate-determining step. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Synthetic Route of 79815-20-6

The Article related to aryl indazole alkenyl preparation diastereoselective regioselective, alkyne aryl indazole alkenylation manganese catalyst, Heterocyclic Compounds (More Than One Hetero Atom): Other 5-Membered Rings, Two Or More Hetero Atoms and other aspects.Synthetic Route of 79815-20-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On June 30, 2008, Brochu, Jean-Louis; Prakesch, Michael; Enright, Gary D.; Leek, Donald M.; Arya, Prabhat published an article.Quality Control of H-Idc-OH The title of the article was Reagent-Based, Modular, Tandem Michael Approach for Obtaining Different Indoline Alkaloid-Inspired Polycyclic Architectures. And the article contained the following:

A modular, reagent-based approach to obtain different indoline alkaloid-inspired, tetracyclic architectures is developed. When TBSOTf was used as a Lewis acid, a tandem Michael-based approach resulted in formation of a diastereomeric mixture of tetracyclic derivatives I with two addnl. six-membered rings from functionalized indoline II. By simply changing the Lewis acid to TMSOTf, II was converted into a different tetracyclic compound III having addnl. functionalized 5- and 7-membered rings with complete stereocontrol. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Quality Control of H-Idc-OH

The Article related to indoline amidoacyl unsaturated preparation tandem intramol michael addition cyclization, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Quality Control of H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On June 18, 2021, Pollastrini, Matteo; Lipparini, Filippo; Pasquinelli, Luca; Balzano, Federica; Barretta, Gloria Uccello; Pescitelli, Gennaro; Angelici, Gaetano published an article.Category: indole-building-block The title of the article was A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives. And the article contained the following:

A thorough exptl. and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Me (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Category: indole-building-block

The Article related to proline mimetic indolinecarboxylic acid derivative amide conformation solvent effect, Physical Organic Chemistry: Resonance Spectra (Electron Spin, Nuclear Magnetic and Fourier Transform Nuclear Magnetic, Quadrupole, etc.) and other aspects.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On November 20, 2002, Sun, Guobin; Pei, Weiwei; Wu, Yongqing; Huo, Jun; Ye, Weiping published an article.Reference of H-Idc-OH The title of the article was Enantioselective borane reduction of prochiral ketones catalyzed by (S)-(indolin-2-yl)methanol or (S)-indoline-2-carboxylic acid. And the article contained the following:

An enantioselective borane reduction of prochiral ketones directly catalyzed by (S)-(indolin-2-yl) methanol or (S)-indoline-2-carboxylic acid was examined and the resultant chiral secondary alcs. with 82% ∼ 87% enantiomeric excess were obtained. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Reference of H-Idc-OH

The Article related to enantioselective borane reduction prochiral ketone catalyzed indolinylmethanol indolinecarboxylic, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Ketones and Derivatives, Including Quinones and Sulfur Analogs and other aspects.Reference of H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On August 9, 2000, Kuwano, Ryoichi; Sato, Koji; Kurokawa, Takashi; Karube, Daisuke; Ito, Yoshihiko published an article.Name: H-Idc-OH The title of the article was Catalytic asymmetric hydrogenation of heteroaromatic compounds, indoles. And the article contained the following:

Indoles I (R = Bu, Me2CHCH2, Ph, MeO2C; R1 = MeCO, Me3COCO; R2 = H, Me, F3C; R3 = H, MeO, F3C) are reduced enantioselectively to nonracemic indolines II in 83-100% yields and 78-95% ee by a rhodium norbornadiene catalyst in the presence of a bis(diphenylphosphinoethyl)biferrocene ligand. E.g., indolecarboxylate I (R = MeO2C; R1 = MeCO; R2 = R3 = H) was stirred in isopropanol in the presence of cesium carbonate, [Rh(norbornadiene)2]+SbF6- and the bis(diphenylphosphinoethyl)biferrocene (S,S)-(R,R)-PhTRAP under hydrogen at 5.0 MPa and at 60° to give II (R = MeO2C; R1 = MeCO; R2 = R3 = H) in 95% yield and 95% ee. The [Rh(norbornadiene)2]+SbF6–(S,S)-(R,R)-PhTRAP catalytic system is the first hydrogenation catalyst found to reduce five-membered heterocyclic systems enantioselectively. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Name: H-Idc-OH

The Article related to indoline enantioselective preparation, indole enantioselective hydrogenation rhodium norbornadiene complex phtrap ligand, catalytic asym hydrogenation heteroaromatic compound and other aspects.Name: H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On August 13, 2007, Friedrich, Anne; Jainta, Manuel; Nieger, Martin; Brase, Stefan published an article.Application of 79815-20-6 The title of the article was One-pot synthesis of symmetrical and unsymmetrical diketopiperazines from unprotected amino acids. And the article contained the following:

An efficient synthesis of sym. and unsym. proline-type diketopiperazines using a phosphite-promoted coupling was used to generate diketopiperazines with overall good yields from unprotected amino acids. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Application of 79815-20-6

The Article related to amino acid autocoupling dimerization amidation cyclization, proline autocoupling dimerization amidation cyclization, ketopiperazine preparation, piperazinedione preparation and other aspects.Application of 79815-20-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On August 14, 2006, Andersson, Fredrik; Hedenstroem, Erik published an article.Recommanded Product: 79815-20-6 The title of the article was Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactions. And the article contained the following:

Two chiral auxiliaries, 2-[(S)-indolin-2-yl]propan-2-ol (I) and (S)-2-(2-methoxypropan-2-yl)indoline, were synthesized from enantiomerically pure (S)-indoline-2-carboxylic acid. High diastereoselectivities in alkylations of enolates of the propanoylamides derived from the two auxiliaries are presented. Surprisingly, both auxiliaries induced the same selectivity at the newly created stereogenic center. The benzyl bromide and Bu iodide alkylation reactions showed diastereomeric ratios that were moderate (81:19) to very good (96:4) and with very good yields (86-98%). When LiCl was used as an enolate coordinating agent, in the benzylation of the enolate from propanoylated auxiliary I, a very high crude diastereomeric ratio was obtained (99.7:0.3). The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Recommanded Product: 79815-20-6

The Article related to acylindolinemethanol chiral auxiliary stereoselective alkylation, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Carboxylic Acids and Peroxycarboxylic Acids and Their Sulfur-Containing Analogs and Salts and other aspects.Recommanded Product: 79815-20-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles