Category: 1416819-91-4

Guan, Yanfei; Ingman, Victoria M.; Rooks, Benjamin J.; Wheeler, Steven E. published the artcile< AARON: An Automated Reaction Optimizer for New Catalysts>, Application In Synthesis of 1416819-91-4, the main research area is transition metal catalytic reaction.

We describe an open-source computational toolkit (AARON: An Automated Reaction Optimizer for New catalysts) that automates the quantum mech. geometry optimization and characterization of the transition state and intermediate structures required to predict the activities and selectivities of asym. catalytic reactions. Modern computational quantum chem. has emerged as a powerful tool for explaining the selectivity and activity of asym. catalysts. However, reliably predicting the stereochem. outcome of realistic reactions often requires the geometry optimization of hundreds of transition state and intermediate structures, which is a tedious process. AARON automates these optimizations through an interface with a popular electronic structure package, accelerating quantum chem. workflows to enable the computational screening of potential catalysts. AARON is built using a collection of object-oriented Perl modules (AaronTools) that provide functionality to build and modify mol. and supramol. structures. The main functionalities of AaronTools are also available as stand-alone command-line scripts. The core features of AaronTools and AARON are explained, and representative applications of AARON to both organocatalyzed and transition-metal-catalyzed reactions are presented.

Journal of Chemical Theory and Computation published new progress about Aryl aldehydes Role: PEP (Physical, Engineering or Chemical Process), PROC (Process). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Hsu, Day-Shin; Wang, Meng-Yu; Huang, Jiun-Yi published the artcile< Asymmetric Total Syntheses of (+)-5-epi-Schisansphenin B and the Proposed Structure of (+)-15-Hydroxyacora-4(14),8-diene>, Reference of 1416819-91-4, the main research area is Heck alkenylation Stetter Tiffeneau Demjanov enantioselective diastereoselective regioselective; epi schisansphenin B total synthesis; hydroxyacoradiene total synthesis.

The asym. total syntheses of (+)-5-epi-schisansphenin B and the proposed structure of (+)-15-hydroxyacora-4(14),8-diene have been accomplished from 1,3-cyclopentadione in eight synthetic steps. The enantioselective palladium-catalyzed redox-relay Heck alkenylation, the intramol. Stetter reaction, and the regioselective Tiffeneau-Demjanov-type ring expansion were the pivotal steps in these syntheses.

Journal of Organic Chemistry published new progress about Alkenylation, stereoselective (redox-relay Heck). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Reference of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Angnes, Ricardo A.; Oliveira, Juliana M.; Oliveira, Caio C.; Martins, Nelson C.; Correia, Carlos Roque D. published the artcile< Stereoselective Synthesis of Aryl Cyclopentene Scaffolds by Heck-Matsuda Desymmetrization of 3-Cyclopentenol>, COA of Formula: C13H15F3N2O, the main research area is arylcyclopentenol diastereoselective enantioselective preparation; arylcyclopentanone enantioselective preparation; Heck Matsuda desymmetrization cyclopentenol aryldiazonium salt palladium pyridinyloxazoline catalyst; diastereoselective enantioselective Heck Matsuda reaction aryldiazonium salt cyclopentenol; bromophenyl chlorophenyl cyclopentenol mol crystal structure; Heck reaction; aryldiazonium salts; chiral N,N ligands; desymmetrization; palladium.

In the presence of palladium bis(trifluoroacetate) and nonracemic (trifluoromethyl)pyridinyloxazoline I, aryldiazonium trifluoroborates RN2+ BF4- [R = 4-MeOC6H4, 2-MeOC6H4, 3,4-(MeO)2C6H3, 3,4,5-(MeO)3C6H2, 4-HOC6H4, 2-HOC6H4, Ph, 4-BrC6H4, 4-ClC6H4, 4-O2NC6H4, 3-O2NC6H4, 2-O2NC6H4, 4-F3CC6H4, 3-F3CC6H4, 2-F3CC6H4] underwent enantioselective Heck-Matsuda desymmetrization reactions with 3-cyclopenten-1-ol to give arylcyclopentenols II [R = 4-MeOC6H4, 2-MeOC6H4, 3,4-(MeO)2C6H3, 3,4,5-(MeO)3C6H2, 4-HOC6H4, 2-HOC6H4, Ph, 4-BrC6H4, 4-ClC6H4, 4-O2NC6H4, 3-O2NC6H4, 2-O2NC6H4, 4-F3CC6H4, 3-F3CC6H4, 2-F3CC6H4] in 20-70% yields and in 85-99% ee and (in some cases) nonracemic 3-arylcyclopentenones in 12-27% yields and in 17-93% ee. The hydroxy group of the cyclopentenol reactant acted as a directing group to control the relative stereochem. of the coupling reaction. The structures of II (R = 4-BrC6H4, 4-ClC6H4) were determined by X-ray crystallog.

Chemistry – A European Journal published new progress about Alcohols, unsaturated Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, COA of Formula: C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Mei, Tian-Sheng; Patel, Harshkumar H.; Sigman, Matthew S. published the artcile< Enantioselective construction of remote quaternary stereocentres>, Quality Control of 1416819-91-4, the main research area is trisubstituted alkenyl alc arylboronic acid palladium relay Heck arylation; aryl carbonyl compound quaternary carbon substituted stereoselective preparation.

Small mols. that contain all-carbon quaternary stereocenters-carbon atoms bonded to four distinct carbon substituents-are found in many secondary metabolites and some pharmaceutical agents. The construction of such compounds in an enantioselective fashion remains a long-standing challenge to synthetic organic chemists. In particular, methods for synthesizing quaternary stereocenters that are remote from other functional groups are underdeveloped. Here we report a catalytic and enantioselective intermol. Heck-type reaction of trisubstituted-alkenyl alcs. with aryl boronic acids. This method provides direct access to quaternary all-carbon-substituted β-, γ-, δ-, ε- or ζ-aryl carbonyl compounds, because the unsaturation of the alkene is relayed to the alc., resulting in the formation of a carbonyl group. The scope of the process also includes incorporation of pre-existing stereocenters along the alkyl chain, which links the alkene and the alc., in which the stereocenter is preserved. The method described allows access to diverse mol. building blocks containing an enantiomerically enriched quaternary center.

Nature (London, United Kingdom) published new progress about Alkenyl alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Quality Control of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Li, Hao; Gao, Ang; Liu, Xiu-Yan; Ding, Chang-Hua; Xu, Bin; Hou, Xue-Long published the artcile< Kinetic Resolution of 5-Substituted Cyclohexenols by Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction>, Name: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is cyclohexenol arylboronic acid palladium catalyst Heck reaction kinetic resolution; aryl cyclohexanone cyclohexenol preparation enantioselective diastereoselective.

The kinetic resolution of 2-substituted-cyclohexenols via palladium-catalyzed asym. redox-relay Heck reaction was realized, providing optically active 2-substituted cyclohexenols and trans-3,5-disubstituted cyclohexan-1-ones in high yield and good enantioselectivities with an S factor up to 22.

Synthesis published new progress about Cyclic ketones Role: BYP (Byproduct), PRP (Properties), PUR (Purification or Recovery), SPN (Synthetic Preparation), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Name: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

de Oliveira Silva, Juliana; Angnes, Ricardo A.; Menezes da Silva, Vitor H.; Servilha, Bruno M.; Adeel, Muhammad; Braga, Ataualpa A. C.; Aponick, Aaron; Correia, Carlos Roque D. published the artcile< Intermolecular Noncovalent Hydroxy-Directed Enantioselective Heck Desymmetrization of Cyclopentenol: Computationally Driven Synthesis of Highly Functionalized cis-4-Arylcyclopentenol Scaffolds>, SDS of cas: 1416819-91-4, the main research area is cyclopentenol aryldiazonium palladium chiral dihydrooxazole enantioselective Heck desymmetrization catalyst; arylcyclopentenol stereoselective preparation.

New computationally driven protocols for the Heck desymmetrization of 3-cyclopenten-1-ol with aryldiazonium tetrafluoroborates were developed. These new conditions furnished remarkable product selectivity originating from a resident hydroxyl group and the critical choice of the reaction solvent. Mechanistic insights gleaned from theor. calculations of the putative transition states predicted toluene as an adequate solvent choice to attain high enantioselectivity by strengthening the noncovalent interaction of the substrate hydroxyl group and the chiral cationic palladium catalyst. Laboratory experiments validated the theor. predictions, and by employing 2% MeOH/toluene as solvent, the Heck-Matsuda reaction provided exclusively the cis-4-arylcyclopentenols in good to excellent yields in enantiomeric excesses up to 99%. The performance of the new PyOx ligand (S)-4-tert-butyl-2-(3,5-dichloropyridin-2-yl)-4,5-dihydrooxazole was also successfully evaluated in the Heck-Matsuda desymmetrization of 3-cyclopenten-1-ol. The synthetic potential of these highly functionalized cis-4-arylcyclopentenols is illustrated by a gold-catalyzed synthesis of cyclopenta[b]benzofuran skeletons.

Journal of Organic Chemistry published new progress about Chiral ligands Role: CAT (Catalyst Use), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, SDS of cas: 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wang, Zhaobin; Yang, Ze-Peng; Fu, Gregory C. published the artcile< Quaternary stereocentres via catalytic enantioconvergent nucleophilic substitution reactions of tertiary alkyl halides>, Reference of 1416819-91-4, the main research area is nickel catalytic enantioconvergent nucleophilic substitution tertiary alkyl electrophiles alkenylzirconium.

The development of efficient methods, particularly catalytic and enantioselective processes, for the construction of all-carbon quaternary stereocentres is an important (and difficult) challenge in organic synthesis due to the occurrence of this motif in a range of bioactive mols. One conceptually straightforward and potentially versatile approach is the catalytic enantioconvergent substitution reaction of a readily available racemic tertiary alkyl electrophile by an organometallic nucleophile; however, examples of such processes are rare. Here we demonstrate that a nickel-based chiral catalyst achieves enantioconvergent couplings of a variety of tertiary electrophiles (cyclic and acyclic α-halocarbonyl compounds) with alkenylmetal nucleophiles to form quaternary stereocentres with good yield and enantioselectivity under mild conditions in the presence of a range of functional groups. These couplings, which probably proceed via a radical pathway, provide access to an array of useful families of organic compounds, including intermediates in the total synthesis of two natural products, (-)-eburnamonine and madindoline A.

Nature Chemistry published new progress about Alkenylation catalysts, stereoselective. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Reference of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Race, Nicholas J.; Yuan, Qianjia; Sigman, Matthew S. published the artcile< Enantioselective C2-Alkylation of Indoles through a Redox-Relay Heck Reaction of 2-Indole Triflates>, Related Products of 1416819-91-4, the main research area is enantioselective alkylation indole Heck triflate; Heck reaction; asymmetric catalysis; enantioselective catalysis; indole; palladium.

A palladium-catalyzed enantioselective redox-relay Heck reaction of 2-indole triflates and disubstituted alkenes is reported. This process combines readily available indole triflates with a variety of alkenes to afford a range of indole derivatives bearing a stereocenter adjacent to C2. Enantioselectivity is achieved through use of a simple pyridine-oxazoline ligand. Tuning the electronics of the indole, through judicious choice of N-protecting group, is required to ensure selective β-hydride elimination away from the indole core. Utility of this method is highlighted in a modular formal synthesis of an S1P1 agonist precursor developed by Merck.

Chemistry – A European Journal published new progress about Alkylation. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Related Products of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

He, Yu-Ping; Cao, Jian; Wu, Hua; Wang, Qian; Zhu, Jieping published the artcile< Catalytic Enantioselective Aminopalladation-Heck Cascade>, Application In Synthesis of 1416819-91-4, the main research area is alkynylaniline cyclopentene diastereoselective enantioselective palladium pyrox aminopalladation Heck cascade; indole cyclopentene stereoselective preparation; asymmetric synthesis; domino reactions; homogeneous catalysis; nucleopalladation; oxidative Heck reactions.

Domino processes initiated by intramol. nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized heterocycles. However, a catalytic enantioselective version of this class of reactions remains scarce. We report herein that reaction of 2-alkynylanilines with prochiral cyclopentenes in the presence of a catalytic amount of Pd(OAc)2, a chiral bidentate pyrox ligand and O2 as terminal oxidant affords the structurally diverse indole-cyclopentene conjugates, e.g., I, bearing two stereocenters in a highly diastereo- and enantio-selective manner. One of the products is converted to a heavily functionalized tetracyclic indolinone derivative

Angewandte Chemie, International Edition published new progress about Addition reaction, aminopalladation. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Xu, Si-Yu; Zhang, Rui; Zhang, Shu-Sheng; Feng, Chen-Guo published the artcile< Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction>, Recommanded Product: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is arylphthalide preparation enantioselective nickel catalyst; bromophthalide arylboronic acid Suzukimiiyaura crosscoupling reaction.

A nickel-catalyzed asym. Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.

Organic & Biomolecular Chemistry published new progress about Arylboronic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Recommanded Product: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem