Tag: M.W=150-200

Ye, Chen-Xi published the artcileStereocontrolled 1,3-nitrogen migration to access chiral α-amino acids, Application In Synthesis of 104-01-8, the main research area is chiral amino acid preparation regioselective enantioselective; azanyl ester preparation amination ruthenium iron catalyst; carboxylic acid hydroxylamine coupling reaction.

Here a protocol for the economical and practical synthesis of optically active α-amino acids RNHC(R1)(R2)C(O)OH (R = Ts, Ms, C(O)OMe, (2,2,2-trichloroethoxy)carbonyl; R1 = H, Me; R2 = pent-2-yn-1-yl, 4-methylphenyl, 2H-1,3-benzodioxol-5-yl, etc.) based on an unprecedented stereocontrolled 1,3-nitrogen shift was reported. The method employs abundant and easily accessible carboxylic acids R1CH(R2)C(O)OH as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalyzed C(sp3)-H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.

Nature Chemistry published new progress about Amination catalysts (regio-, stereoselective). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application In Synthesis of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Hilpert, Lukas J. published the artcileRhodium-Catalyzed Parallel Kinetic Resolution of Racemic Internal Allenes Towards Enantiopure Allylic 1,3-Diketones, Category: isoquinoline, the main research area is allene diketone parallel kinetic resolution rhodium enantioselective addition catalyst; allylic diketone enantiopure stereoselective preparation; 1,3-diketones; allenes; asymmetric catalysis; parallel kinetic resolution; rhodium.

A rare case of a parallel kinetic resolution of racemic 1,3-disubstituted allenes by means of a rhodium-catalyzed addition to 1,3-diketones furnishing enantiopure allylic 1,3-diketones is described. Mechanistic experiments demonstrate that the different allene enantiomers react in parallel to either the diastereomeric E- or Z-allylic 1,3-diketones with the same absolute configuration of the newly formed stereogenic center. A broad substrate scope demonstrates the synthetic utility of this new method.

Angewandte Chemie, International Edition published new progress about Addition reaction catalysts, stereoselective. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Trost, Barry M. published the artcileBranched aldehydes as linchpins for the enantioselective and stereodivergent synthesis of 1,3-aminoalcohols featuring a quaternary stereocenter, Application of 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, the main research area is aminoalc preparation enantioselective diastereoselective; aldehyde Mannich aldol Henry alkyne addition zinc prophenol catalyst.

The use of branched aldehydes e.g., benzyl (S)-(1-(4-fluorophenyl)-2,2-dimethyl-3-oxopropyl)carbamate as versatile linchpins for various Zn-prophenol-catalyzed C-C bond-forming reactions to efficiently construct enantioenriched 1,3-aminoalcs. e.g., I bearing an acyclic quaternary stereogenic center was reported. The ability of the Zn-ProPhenol catalyst to selectively activate ambiphilic aldehydes first as nucleophiles for Mannich reactions and then as electrophiles for aldol, Henry and alkyne addition reactions allows for the one-pot synthesis of complex stereotriads from common building blocks. Moreover, this approach can be diastereodivergent by simply selecting the proper catalyst combination. Overall, this catalytic method directly transforms simple and readily available aldehydes into highly functionalized compounds and provides streamlined access to valuable 1,3-aminoalcs. relevant to the synthesis of biol. important mols.

Nature Catalysis published new progress about Addition reaction catalysts, stereoselective. 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Application of 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Hu, Jiang-Lin published the artcileRuthenium-Catalyzed Enantioselective Addition of Carboxylic Acids to Allenes, Category: isoquinoline, the main research area is branched allylic ester enantioselective regioselective preparation; allene carboxylic acid addition ruthenium catalyst.

A ruthenium-catalyzed synthetic method for branched allylic esters I [R1 = TBSO(CH2)2, cyclopentyl, Ph(CH2)2, etc.; R2 = i-Pr, 2-thienyl, Ph, etc.] via addition of carboxylic acids to allenes was reported. Ligands were designed and prepared based on Josiphos skeleton, with which reaction achieved up to 95% yield and up to >99% enantiomeric excess. A deuterium labeling experiment was performed and a plausible mechanism was proposed. Enantiopure lactones of five- and six-membered ring were synthesized via a RCM reaction of branched allylic ester product.

ACS Catalysis published new progress about Addition reaction catalysts, stereoselective. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Jiang, Yuqi published the artcileDiscovery of Second-Generation NLRP3 Inflammasome Inhibitors: Design, Synthesis, and Biological Characterization, Formula: C9H10O3, the main research area is preparation NLRP3 inflammasome inhibitor.

NLRP3 inflammasomes have recently emerged as an attractive drug target for neurodegenerative disorders. In our continuing studies, a new chem. scaffold was designed as selective inhibitors of NLRP3 inflammasomes. Initial characterization of the lead HL16 demonstrated improved, however, nonselective inhibition on the NLRP3 inflammasome. Structure-activity relationship studies of HL16 identified a new lead, 17 (YQ128), with an IC50 of 0.30 ± 0.01μM. Further studies from in vitro and in vivo models confirmed its selective inhibition on the NLRP3 inflammasome and its brain penetration. Furthermore, pharmacokinetic studies in rats at 20 mg/kg indicated extensive systemic clearance and tissue distribution, leading to a half-life of 6.6 h. However, the oral bioavailability is estimated to be only 10%, which may reflect limited GI permeability and possibly high first-pass effects. Collectively, these findings strongly encourage development of more potent analogs with improved pharmacokinetic properties from this new chem. scaffold.

Journal of Medicinal Chemistry published new progress about Central nervous system agents (potential as). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Mase, Nobuyuki published the artcileSynthesis of β-hydroxyaldehydes with stereogenic quaternary carbon centers by direct organocatalytic asymmetric aldol reactions, Recommanded Product: 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, the main research area is asym aldol reaction aldehyde chiral amine acid catalyst.

A fluorescence detection system was used to identify effective chiral amine/acid combinations as bifunctional catalysts for asym. direct catalytic aldol reactions of α,α-dialkyl aldehydes with aryl aldehydes. With the optimized catalyst system, the reaction of isobutyraldehyde with p-nitrobenzaldehyde provided the α,α-di-Me aldol product in 92% yield with 96% ee.

Angewandte Chemie, International Edition published new progress about Acids Role: CAT (Catalyst Use), USES (Uses). 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Recommanded Product: 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kim, Byungjun published the artcileStereodivergent Carbon-Carbon Bond Formation between Iminium and Enolate Intermediates by Synergistic Organocatalysis, Category: isoquinoline, the main research area is iminium enolate Michael addition.

Herein a stereodivergent method for the Michael addition of aryl acetic acid esters to α,β-unsaturated aldehydes catalyzed by a combination of a chiral pyrrolidine and a chiral Lewis base has been reported. This reaction proceeds through a synergistic catalytic cycle which consists of one cycle leading to a chiral iminium electrophile and a second cycle generating a nucleophilic chiral enolate for the construction of a carbon-carbon bond. By varying the combinations of catalyst enantiomers, all four stereoisomers of the products with two vicinal stereocenters are accessible with high enantio- and diastereoselectivity. The products of the Michael addition, 1,5-aldehyde esters, can be readily transformed into a variety of other valuable enantioenriched structures, including those bearing three contiguous stereocenters in an acyclic system, thus providing an efficient route to an array of structural and stereochem. diversity.

Journal of the American Chemical Society published new progress about Michael reaction catalysts, stereoselective. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Bourgeois, Frederic published the artcileCatalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands, SDS of cas: 1205-17-0, the main research area is hydroxy butyrolactone preparation enantioselective; aldehyde ethyl glyoxylate aldol addition transfer hydrogenation.

A catalyst repurposing strategy based on a sequential aldol addition and transfer hydrogenation giving access to enantiomerically enriched α-hydroxy-γ-butyrolactones is described. The combination of a stereoselective, organocatalytic step, followed by an efficient catalytic aldehyde reduction induces an ensuing lactonization to provide enantioenriched butyrolactones from readily available starting materials. By capitalizing from the capacity of prolineamides to act as both an organocatalyst and a transfer hydrogenation ligand, catalyst repurposing allowed the development of an operationally simple, economic, and efficient sequential catalysis approach.

Organic Letters published new progress about Aldol addition catalysts, stereoselective. 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, SDS of cas: 1205-17-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zhang, Yu-Lan published the artcileVinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation, Application In Synthesis of 104-01-8, the main research area is vinyl sulfonium salt radical acceptor decarboxylative alkenylation.

Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl radical precursor, metal-free decarboxylative alkenylation with vinyl sulfonium salts was realized using eosin Y as a photocatalyst. This process features a broad substrate scope and tolerates a broad range of primary, secondary, tertiary carboxylic acids.

Organic Letters published new progress about Alkenylation catalysts, stereoselective (photochem.). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application In Synthesis of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Xin-Ran published the artcileControllable Tandem [3+2] Cyclization of Aromatic Aldehydes with Maleimides: Rhodium(III)-Catalyzed Divergent Synthesis of Indane-Fused Pyrrolidine-2,5-dione, SDS of cas: 86-51-1, the main research area is indane fused pyrrolidinedione diastereoselective synthesis tandem cyclization aldehyde maleimide.

Controllable rhodium(III)-catalyzed tandem [3+2] cyclization of aromatic aldehydes with maleimides is developed for the divergent synthesis of stereoselective indane-fused pyrrolidine-2,5-dione. Switchable access to different products could be achieved by employing different additives and varying the reaction time. This atom-economic transformation proceeds efficiently via the C-H bond activation directed by weakly coordinating aldehydes and is characterized by exclusive stereoselectivity, air atm., and being free of nitrogen-based transient directing groups.

Organic Letters published new progress about 1,3-Dipolar cycloaddition reaction, stereoselective. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, SDS of cas: 86-51-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem