Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(24), P. 7136 - 7148
Published: Jan. 1, 2023
DFT calculations disclosed that the central functional group could induce a favorable chiral environment and determine enantioselectivity for Brønsted C–H acid catalysis.
Language: Английский
Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(18)
Published: Aug. 2, 2023
Abstract A facile enantioselective alkynylation of cyclic ketimines attached to a neutral functional group utilizing the dual Cu(I)‐CPA catalysis is described. The strategy 2‐aryl‐3 H ‐indol‐3‐one directly chiral propargylic amines containing indolin‐3‐one moiety in good yields and enantioselectivities. Moreover, gram‐scale synthesis propargylamines based C2‐quaternary indolin‐3‐ones was performed. synthetic applications were confirmed by transformations products with no decrease yield enantioselectivity.
Language: Английский
Citations
4
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
A direct asymmetric synthesis of α-(3-pyrrolyl)methanamines has been developed for the first time with good yields and excellent enantioselectivity under mild conditions by avoiding protection–deprotection chemistry.
Language: Английский
Citations
1
Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1319, P. 139373 - 139373
Published: July 26, 2024
Language: Английский
Citations
1
Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)
Published: July 6, 2023
Abstract Indol‐3‐ones are readily available reaction substrates, but their utility in asymmetric reactions is underdeveloped. Herein, we describe the organocatalytic aza‐Friedel‐Crafts‐type of indol‐3‐ones with 1‐ and 2‐naphthols. By using spirocyclic chiral phosphoric acids quinine‐incorporated squaramides as organocatalysts, two classes structurally distinct compounds, namely 2‐(hydroxylnaphthyl)‐indolin‐3‐ones tetrahydrofuroindoles, formed respectively. These quaternary centre‐containing indoline derivatives may find use synthesis biologically active molecules.
Language: Английский
Citations
3
European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(35)
Published: July 27, 2023
Abstract A Friedel–Crafts reaction of indolizines with 2‐aryl‐3 H ‐indol‐3‐ones catalyzed by B(C 6 F 5 ) 3 is described. This protocol gives access to indolizine derivatives that are valuable building blocks in synthetic and pharmaceutical chemistry. The proceeds under mild conditions, affording various C2‐quaternary indolin‐3‐ones based on high yields regioselectivities. Moreover, the transformations target products were realized N‐methylation trifluoromethane sulfonation.
Language: Английский
Citations
1
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(31)
Published: June 7, 2024
Abstract Here, we have successfully achieved the addition of difluoroacetate radicals to 2‐aryl‐3 H ‐indol‐3‐ones, enabling various difluoroalkylations C2‐tetrasubstituted 2‐aryl indolin‐3‐ones in a highly efficient and economical manner. It is worth mentioning that these difluoroalkylation compounds can be easily transformed into derivatives under mild reaction conditions. Control experiments suggest involvement ethyl radical species reaction.
Language: Английский
Citations
0
Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 15, 2024
Abstract Due to its structural complexity and intrinsic sensitivity of bridged aminal junction, 2,6‐diazabicyclo[2.2.2]octane (2,6‐DABCO) has remained a highly desirable target in synthetic chemistry. However, the asymmetric access this unit is still insufficient hampered by need for meticulously created functionalities intricate double aza‐cyclizations. Herein, we have developed novel enantio‐ diastereoselective protocol polycyclic chiral 2,6‐DABCOs under metal‐free conditions. This domino process involves amine‐catalyzed [4+2] annulation between glutaraldehyde 2‐arylindol‐3‐ones, followed an acid‐mediated Pictet–Spengler reaction/intramolecular aza‐cyclization cascade sequence with tryptamine trapping situ generated 3‐oxindolium ion intermediate first time. Overall, fused medicinally relevant scaffolds were isolated good yield excellent stereoselectivity constructing five new bonds four stereocenters one‐pot operation.
Language: Английский
Citations
0
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 15, 2024
Due to its structural complexity and intrinsic sensitivity of bridged aminal junction, 2,6-diazabicyclo[2.2.2]octane (2,6-DABCO) has remained a highly desirable target in synthetic chemistry. However, the asymmetric access this unit is still insufficient hampered by need for meticulously created functionalities intricate double aza-cyclizations. Herein, we have developed novel enantio- diastereoselective protocol polycyclic chiral 2,6-DABCOs under metal-free conditions. This domino process involves amine-catalyzed [4+2] annulation between glutaraldehyde 2-arylindol-3-ones, followed an acid-mediated Pictet-Spengler reaction/intramolecular aza-cyclization cascade sequence with tryptamine trapping situ generated 3-oxindolium ion intermediate first time. Overall, fused medicinally relevant scaffolds were isolated good yield excellent stereoselectivity constructing five new bonds four stereocenters one-pot operation.
Language: Английский
Citations
0
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 11, 2024
Abstract Among the nucleophilic oxidants employed in gold‐catalysed oxidation of alkynes, sulphur‐based reagents have played a substantial role since beginning, granting access to respective gold carbene intermediates. Herein, we describe first example substance class sulfoximines being used as atom transfer alkynes catalysis. Based on transformation N ‐(2‐alkynylphenyl) 3 H ‐indol‐3‐ones, it is demonstrated that sulfoximine functionality capable selectively transferring its nitrogen moiety alkyne, forming α‐imino carbene, which then oxidised by released sulfoxide second step via pseudo‐intramolecular mechanism—a distinctive feature differentiates this work mechanistically from earlier studies. A combination extensive experimental and theoretical studies provides evidence for mechanistic rationale. As no external 1,2‐difunctionalisation alkyne unit are required, wide variety functional groups tolerated transformation, affording desired ‐indol‐3‐ones mostly good yields. It was further also showcased possible combine our methodology with additional transformations ‐indol‐3‐one core one‐pot procedures, allowing facile C2‐quaternary indolin‐3‐one structures.
Language: Английский
Citations
0
Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 11, 2024
Abstract Unter den nukleophilen Oxidationsmitteln, die bei der goldkatalysierten Oxidation von Alkinen eingesetzt werden, haben schwefelbasierte Reagenzien Beginn an eine wesentliche Rolle gespielt und ermöglichten Zugang zu jeweiligen Goldcarben Intermediaten. Wir beschreiben hier das erste Beispiel für Verwendung Substanzklasse Sulfoximine als Atomtransferreagenzien in Goldkatalyse. Anhand Umwandlung N ‐(2‐Alkinylphenyl)‐sulfoximinen 3 H ‐Indol‐3‐onen wird gezeigt, dass Sulfoximinfunktionalität dazu Lage ist, unter Ausbildung des α‐Imino‐Goldcarbens zunächst Stickstoffeinheit selektiv auf Alkin übertragen, welches dann einem zweiten Schritt durch freigesetzte Sulfoxid pseudo‐intramolekularen Mechanismus oxidiert ‐ Besonderheit, diese Arbeit mechanistisch früheren Studien unterscheidet. Eine Kombination aus umfangreichen experimentellen theoretischen liefert Beweise zugrundeliegenden Mechanismus. Da keine externen 1,2‐Difunktionalisierung Alkins erforderlich sind, Vielzahl funktioneller Gruppen toleriert, so gewünschten ‐Indol‐3‐one meist guter Ausbeute erhalten werden. Darüber hinaus wurde es möglich unsere Methodik mit weiteren Transformationen ‐Indol‐3‐on Kerns Eintopfverfahren kombinieren, was einen einfachen C2‐quartären Indolin‐3‐on Strukturen ermöglicht.
Citations
0