Chiral guanidine catalyzed Michael addition reaction and Diels-Alder reaction of anthrone and N-methylmaleimide

2010 ◽  
Vol 18 (3) ◽  
pp. 411-413 ◽  
Author(s):  
Peng Bin ◽  
Cheng Ke-Jun ◽  
Ma Da-Wei
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Michael Addition Reaction ◽  
Diels Alder Reaction

scholarly journals A Bidentate iodine(III)-Based Halogen Bond Donor as Powerful Organocatalyst

2020 ◽  
Author(s):  
Flemming Heinen ◽  
Dominik Reinhard ◽  
Elric Engelage ◽  
Stefan Huber
Keyword(s):  
Lewis Acids ◽  
Addition Reaction ◽  
Halogen Bond ◽  
Alder Reaction ◽  
Diels Alder ◽  
Michael Addition Reaction ◽  
Bidentate Coordination ◽  
Diels Alder Reaction ◽  
The One ◽  
System Approaches

<div>In contrast to iodine(I)-based halogen bond donors, </div><div>iodine(III)-derived ones have only been used as Lewis acidic organocatalysts in a handful of examples, and in all cases they acted in a monodentate fashion. Herein, we report the first application of a bidentate bis(iodolium) salt as organocatalyst in a Michael and a nitro-Michael addition reaction as well as in a Diels-Alder reaction that had not been activated by noncovalent organocatalysts before. In all cases, the performance of this bidentate XB donor distinctly </div><div>surpassed the one of arguably the currently strongest iodine(I)-based organocatalyst. Bidentate coordination to the substrate was corroborated by a structural analysis and by DFT calculations of the transition states. Overall, the catalytic activity of the bis(iodolium) system approaches that of strong Lewis acids like BF3.</div>

scholarly journals A Bidentate iodine(III)-Based Halogen Bond Donor as Powerful Organocatalyst

2020 ◽  
Author(s):  
Flemming Heinen ◽  
Dominik Reinhard ◽  
Elric Engelage ◽  
Stefan Huber
Keyword(s):  
Lewis Acids ◽  
Addition Reaction ◽  
Halogen Bond ◽  
Alder Reaction ◽  
Diels Alder ◽  
Michael Addition Reaction ◽  
Bidentate Coordination ◽  
Diels Alder Reaction ◽  
The One ◽  
System Approaches

<div>In contrast to iodine(I)-based halogen bond donors, </div><div>iodine(III)-derived ones have only been used as Lewis acidic organocatalysts in a handful of examples, and in all cases they acted in a monodentate fashion. Herein, we report the first application of a bidentate bis(iodolium) salt as organocatalyst in a Michael and a nitro-Michael addition reaction as well as in a Diels-Alder reaction that had not been activated by noncovalent organocatalysts before. In all cases, the performance of this bidentate XB donor distinctly </div><div>surpassed the one of arguably the currently strongest iodine(I)-based organocatalyst. Bidentate coordination to the substrate was corroborated by a structural analysis and by DFT calculations of the transition states. Overall, the catalytic activity of the bis(iodolium) system approaches that of strong Lewis acids like BF3.</div>

scholarly journals Aqueous phase fly-ash catalyzed [4+2] Diels-Alder reaction of aryl enones and cyclopentadiene: Synthesis and insect antifeedant activities of aryl bicyclo [2.2.1] heptene-2-yl-methanones

2014 ◽  
Vol 69 (1-2) ◽  
Author(s):  
G. Thirunarayanan
Keyword(s):  
Fly Ash ◽  
Spectral Data ◽  
Aqueous Phase ◽  
Addition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Leaf Discs ◽  
Physical Constants ◽  
Bioassay Method ◽  
Diels Alder Reaction

AbstractA series containing ten aryl 3-(substituted phenyl) bicyclo [2.2.1] heptene-2-yl-methanone derivatives including 3- (substituted phenyl) bicyclo [2.2.1]hepten-2-yl-(pyren-1-yl)- methanones have been synthesized by aqueous phase fly-ash catalyzed [4+2] Diels-Alder cyclo addition reaction of cyclopentadiene and aryl chalcones. The yields of the methanones are more than 60%. The synthesized methanones are characterized by their physical constants and spectral data. The insect antifeedant activities of synthesized methanones have been studied using Dethler’s leaf-discs bioassay method.

Self-crosslinkable polymers from furan-functionalized Meldrum's acid and maleimides as effective precursors of free-standing and flexible crosslinked polymer films showing low dielectric constants

2020 ◽  
Vol 11 (9) ◽  
pp. 1606-1613 ◽  
Author(s):  
Chien-Ho Huang ◽  
Ying-Ling Liu
Keyword(s):  
Polymer Films ◽  
Michael Addition ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dielectric Constants ◽  
Free Standing ◽  
Crosslinked Polymer ◽  
Low Dielectric ◽  
Diels Alder Reaction ◽  
Reactive Polymers

The integration of Michael addition and Diels–Alder reaction in the synthesis of reactive polymers for self-standing and flexible crosslinked polymer films.

Multiple Activation Catalyst for Asymmetric [4+2] Cycloaddition of Aldehydes with Dienes

Synlett ◽  
2021 ◽  
Author(s):  
Takuya Kurahashi ◽  
Seijiro Matsubara ◽  
Rei Tomifuji ◽  
Shunpei Murano ◽  
Satoru Teranishi ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Addition Reaction ◽  
Catalyst System ◽  
Alder Reaction ◽  
Diels Alder ◽  
Functional Theory ◽  
Diels Alder Reaction ◽  
Chiral Phosphoric Acid ◽  
High Yields

AbstractThe enantioselective oxa-Diels–Alder reaction of nonactivated substrates by utilizing FeCl3 and a 1,1′-bi-2-naphthol (BINOL) derived chiral phosphoric acid as a multiple activation catalyst is reported. Various oxygen-containing six-membered heterocycles were obtained in high yields and in an enantioselective manner. Density functional theory (DFT) calculations elucidate that both Lewis acidic and Brønsted acidic moieties in the catalyst system synergistically activate two lone pairs of an aldehyde to facilitate enantioselective addition reaction of dienes.

A Diels-Alder reaction / oxa-Michael addition / acyloin rearrangement cascade on tropolonic substrates

2018 ◽  
Vol 59 (16) ◽  
pp. 1560-1563 ◽  
Author(s):  
Macarena Eugui ◽  
Katerine Rasquin ◽  
Andrés López Radcenco ◽  
Leopoldo Suescun ◽  
Guillermo Moyna
Keyword(s):  
Michael Addition ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Organocatalyzed Thia-Michael Addition and Sequential Inverse Electron Demanding Diels-Alder Reaction to 3-Vinyl-1,2,4- triazine Platforms

2017 ◽  
Vol 359 (23) ◽  
pp. 4106-4110 ◽  
Author(s):  
Clément Berthonneau ◽  
Floris Buttard ◽  
Marie-Aude Hiebel ◽  
Franck Suzenet ◽  
Jean-François Brière
Keyword(s):  
Michael Addition ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit 4nπ- und (4n+2)π-Elektronen, XVII [1] Diels-Aider- und Michael-Additionsreaktionen von 3-Alkoxy-2,4-dihydropyrrolo[3,4-b]indolen mit Ethindicarbonsäuredialkylestern / Structure and Reactivity of Isoannelated Heterocyclic Systems with 4nπ- and (4n+2)π-Electrons, XVII [1] Diels-Alder and Michael Addition Reactions of 3-Alkoxy-2,4-dihydropyrrolo[3,4-b]indoles with Dialkyl Acetylenedicarboxylates

1988 ◽  
Vol 43 (12) ◽  
pp. 1656-1661 ◽  
Author(s):  
Gerald Dyker ◽  
Richard P. Kreher
Keyword(s):  
Michael Addition ◽  
Isotopic Labeling ◽  
Alder Reaction ◽  
Diels Alder ◽  
Addition Reactions ◽  
Current Interest ◽  
Polar Solvents ◽  
Dialkyl Acetylenedicarboxylates ◽  
Diels Alder Reaction

Abstract The reactions of 2-rm-butyl-3-methoxy-4-methyl-2,4-dihydropyrrolo[3,4-b]indole (3) with dialkyl acetylenedicarboxylates are decisively influenced by the solvent. In the presence of alcohols as protic and polar solvents Michael addition is prefered, while in aprotic and less polar solvents like ether the Diels-Alder reaction is favoured. Based on stereospecific hydrolysis and isotopic labeling dipolar intermediates are discussed. The results are of current interest for mechanistic and theoretical reasons

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