Search results

article

Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides with 2,4‐Dienals: Construction of Remote Stereogenic Centers via 1,6‐Addition Reaction

Hui Jiang, Leijie Zhou, Biming Mao, Chunhao Yuan, more

Advanced Synthesis & Catalysis > 362 > 24 > 5716 - 5720

A regio‐ and stereoselective [3+2] cycloaddition of phthalazinium dicyanomethanides with 2,4‐dienals was achieved with the use of a commercially available MacMillan's calalyst via LUMO‐lowering activation. The reaction proceeds through 1,6‐additon to linear 2,4‐dienals with remote control over stereochemistry, affording the cycloadducts having three stereogenic centers.

article

Polyenals and Polyenones in Aminocatalysis: A Decade Building Complex Frameworks from Simple Blocks

Tushar Janardan Pawar, Suhas Balasaheb Mitkari, Eduardo Peña‐Cabrera, Clarisa Villegas Gómez, more

European Journal of Organic Chemistry > 2020 > 38 > 6044 - 6061

Polyenals and polyenones are simple chemical compounds which can be constructed into large and complex structures by virtue of aminocatalysis. In the past eight years, new aminocatalytic activation modes based on trienamine, cross‐trienamine, tetraenamine, iminium ion, and vinylogous iminium ion intermediates have attracted great attention in the field of asymmetric synthesis. Key to the increasing...

article

Cross‐conjugated Trienamine Catalysis with α′‐Alkylidene 2‐Cyclohexenones: Application in β,γ‐Regioselective Aza‐Diels–Alder Reaction

Zhi Zhou, Zhou‐Xiang Wang, Qin Ouyang, Wei Xiao, more

Chemistry – A European Journal > 23 > 12 > 2945 - 2949

Endo‐type cross‐conjugated trienamines between highly congested α′‐alkylidene 2‐cyclohexenones and a chiral primary amine catalyst serve as HOMO‐raised dienophiles in inverse‐electron‐demand aza‐Diels–Alder cycloadditions with a number of 1‐azadiene substrates. The reactions exhibit exclusive β,γ‐regioselectivity, and multifunctional products with high molecular complexity are efficiently constructed...

article

Aminocatalytic asymmetric Diels–Alder reaction of phosphorus dienophiles and 2,4-dienals

Qing-Qing Zhou, Xin Yuan, You-Cai Xiao, Lin Dong, more

Tetrahedron > 2013 > 69 > 48 > 10369- 10374

Chiral compounds bearing a phosphorus functional group are valuable because of their wide application in biological studies and asymmetric catalysis. Here we present an asymmetric Diels–Alder cycloaddition between phosphor-containing dienophiles and 2,4-dienals under the catalysis of chiral amine 1 via the intermediacy of trienamine species (trienamine catalysis). A spectrum of densely functionalized...

article

A Concise Assembly of Electron‐Deficient 2,4‐Dienes and 2,4‐Dienals: Regio‐ and Stereoselective exo‐Diels–Alder and Redox Reactions through Sequential Amine and Carbene Catalysis

Chao Ma, Zhi‐Jun Jia, Jing‐Xin Liu, Qing‐Qing Zhou, more

Angewandte Chemie > 125 > 3 > 982 - 985

Trienamin‐Aktivierung wurde für die Entwicklung einer γ,δ‐regioselektiven Diels‐Alder‐Reaktion mit elektronenarmen β‐substituierten 2,4‐Dienen und 2,4‐Dienalen genutzt. Die resultierenden multifunktionellen Cycloaddukte enthalten perfekt positionierte funktionelle Gruppen, wodurch ein 1,5‐Hydridtransfer von der C‐H‐Gruppe eines Aldehyds an ein aktiviertes Alken unter sequenzieller Katalyse eines Carbens...

article

A Concise Assembly of Electron‐Deficient 2,4‐Dienes and 2,4‐Dienals: Regio‐ and Stereoselective exo‐Diels–Alder and Redox Reactions through Sequential Amine and Carbene Catalysis

Chao Ma, Zhi‐Jun Jia, Jing‐Xin Liu, Qing‐Qing Zhou, more

Angewandte Chemie International Edition > 52 > 3 > 948 - 951

Ideal relay catalysis: A γ,δ‐regioselective anomalous exo‐Diels–Alder reaction with electron‐deficient β‐substituted 2,4‐dienes and 2,4‐dienals has been developed by using trienamine activation. The resulting multifunctional cycloadducts contain perfectly positioned functional groups, thereby facilitating a 1,5‐hydride transfer from the C–H group of an aldehyde to an activated alkene under sequential...

article

Trienamines: Their Key Role in Extended Organocatalysis for Diels-Alder Reactions

Silvia Reboredo, Alejandro Parra, José Alemán

Asymmetric Catalysis > 2013 > 1 > 1

Activation via trienamine intermediates is a synthetically useful protocol for performing asymmetric Diels-Alder reactions controlled by a remote chiral catalyst (a secondary or primary amine). Key features underpinning this concept are the conformation towards the trienamine formation and also the use of highly electrophilic dienophiles. This cycloaddition reaction allows the application of asymmetric...

article

Enantioselective H‐Bond‐Directing Approach for Trienamine‐mediated Reactions in Asymmetric Synthesis

Łukasz Albrecht, Fabio Cruz Acosta, Alberto Fraile, Anna Albrecht, more

Angewandte Chemie > 124 > 36 > 9222 - 9226

In die richtige Richtung: Die vorgestellte enantioselektive Synthese von funktionalisierten Tetrahydroxanthonen basiert auf einer Trienamin‐vermittelten Cycloaddition zwischen 2,4‐Dienalen und aktivierten Chromonen. Die Kontrolle des stereochemischen Ausgangs der Reaktion wird durch Einsatz eines H‐Brücken‐dirigierenden Aminokatalysators ermöglicht.

article

Erweiterung der Strategie zur aminokatalytischen Aktivierung durch HOMO‐Anhebung: Wo ist die Grenze?

Elena Arceo, Paolo Melchiorre

Angewandte Chemie > 124 > 22 > 5384 - 5386

Immer weiter entfernte Stereozentren werden in der asymmetrischen Aminokatalyse angepeilt. Die Anwendung des Konzepts der HOMO‐Anhebung auf δ,δ‐disubstituierte 2,4‐Dienone verdeutlicht das Potenzial der Trienaminstrategie. Mit einem primären Cinchona‐Aminkatalysator gelingt damit eine hoch selektive asymmetrische Diels‐Alder‐Reaktion von Enonen mit elektronenarmen Dienophilen (siehe Schema; TFA=Trifluoressigsäure).

article

Titelbild: Trienamine Catalysis with 2,4‐Dienones: Development and Application in Asymmetric Diels–Alder Reactions (Angew. Chem. 18/2012)

Xiao‐Feng Xiong, Quan Zhou, Jing Gu, Lin Dong, more

Angewandte Chemie > 124 > 18 > 4315 - 4315

Eine asymmetrische Diels‐Alder‐Cycloaddition von δ,δ‐disubstituierten 2,4‐Dienonen unter Trienaminkatalyse an primäre Amine auf Cinchona‐Basis wurde entwickelt. In der Zuschrift auf S. 4477 ff. zeigen Y.‐C. Chen et al., dass zahlreiche elektronenarme Dienophile an dieser Reaktion teilnehmen und mit ausgezeichneter Stereoselektivität hoch funktionalisierte Cyclohexene liefern.

article

Trienamine Catalysis with 2,4‐Dienones: Development and Application in Asymmetric Diels–Alder Reactions

Xiao‐Feng Xiong, Quan Zhou, Jing Gu, Lin Dong, more

Angewandte Chemie > 124 > 18 > 4477 - 4480

Multifunktionelle Cyclohexenderivate entstehen bei einer asymmetrischen Diels‐Alder‐Cycloaddition von δ,δ‐disubstituierten 2,4‐Dienonen, die über Trienaminkatalyse unter Verwendung primärer Cinchona‐Amine abläuft (siehe Schema). Elektronenarme Dienophile wie N‐substituierte Maleimide und 3‐Alkenyloxindole wurde umgesetzt, und die Cyclohexene wurden mit ausgezeichneter Stereoselektivität und hohem...

INFONA - science communication portal

Search results

Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides with 2,4‐Dienals: Construction of Remote Stereogenic Centers via 1,6‐Addition Reaction

Polyenals and Polyenones in Aminocatalysis: A Decade Building Complex Frameworks from Simple Blocks

Cross‐conjugated Trienamine Catalysis with α′‐Alkylidene 2‐Cyclohexenones: Application in β,γ‐Regioselective Aza‐Diels–Alder Reaction

Aminocatalytic asymmetric Diels–Alder reaction of phosphorus dienophiles and 2,4-dienals

A Concise Assembly of Electron‐Deficient 2,4‐Dienes and 2,4‐Dienals: Regio‐ and Stereoselective exo‐Diels–Alder and Redox Reactions through Sequential Amine and Carbene Catalysis

A Concise Assembly of Electron‐Deficient 2,4‐Dienes and 2,4‐Dienals: Regio‐ and Stereoselective exo‐Diels–Alder and Redox Reactions through Sequential Amine and Carbene Catalysis

Trienamines: Their Key Role in Extended Organocatalysis for Diels-Alder Reactions

Enantioselective H‐Bond‐Directing Approach for Trienamine‐mediated Reactions in Asymmetric Synthesis

Erweiterung der Strategie zur aminokatalytischen Aktivierung durch HOMO‐Anhebung: Wo ist die Grenze?

Titelbild: Trienamine Catalysis with 2,4‐Dienones: Development and Application in Asymmetric Diels–Alder Reactions (Angew. Chem. 18/2012)

Trienamine Catalysis with 2,4‐Dienones: Development and Application in Asymmetric Diels–Alder Reactions

Filter options

Publication date

Publication language

Keywords

Data set

INFONA - science communication portal

Search results

Add recipient

Sending message cancelled

Are you sure you want to cancel sending this message?

Send message

Filter options

Publication date

Date range setting

Set the date range to filter the displayed results. You can set a starting date, ending date or both. You can enter the dates manually or choose them from the calendar.

Publication language

Keywords

Data set

Reporting an error / abuse

Sending the report failed

Accessibility options