Reactivity of 7‐Azanorbornenes in Bioorthogonal Inverse Electron‐Demand Diels–Alder Reactions
Sign Up to like & getrecommendations! Published in 2017 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.201700411
Abstract: In the preparation of multicomponent compounds, the accumulation of components through sequential click reactions is an attractive strategy. In this work we examined the reactivity of various N-substituted 7-azanorbornenes in inverse electron-demand Diels–Alder (iEDDA) reactions… read more here.
Keywords: diels alder; demand diels; inverse electron; electron demand ... See more keywords
Porphyrin-based covalent organic polymer by inverse electron demand Diels-Alder reaction
Sign Up to like & getrecommendations! Published in 2021 at "European Polymer Journal"
DOI: 10.1016/j.eurpolymj.2021.110664
Abstract: Abstract Inverse electron demand Diels-Alder (IEDDA) reaction has been employed as a powerful ligation in several fields. In the current work, a synthetic approach relying on IEDDA reaction is developed for preparation of a porphyrin… read more here.
Keywords: diels alder; demand diels; polymer; inverse electron ... See more keywords
Antiaromaticity Gain Activates Tropone and Nonbenzenoid Aromatics as Normal-Electron-Demand Diels-Alder Dienes.
Sign Up to like & getrecommendations! Published in 2020 at "Organic letters"
DOI: 10.1021/acs.orglett.0c02343
Abstract: We propose a carbonyl umpolung strategy for activating tropone as a normal-electron-demand Diels-Alder diene. Tropone has low reactivity for Diels-Alder reactions because of its [4n+2] π-aromaticity. Conversion of the carbonyl group into a hydrazone ion… read more here.
Keywords: diels alder; normal electron; demand diels; electron demand ... See more keywords
Clip to Click: Controlling Inverse Electron-Demand Diels-Alder Reactions with Macrocyclic Tetrazines.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01010
Abstract: A universal strategy to control tetrazine reactivity in the inverse electron-demand Diels-Alder (IEDDA) reaction was developed as "Clip to Click". Incorporating a chemical bridge into 3,6-diphenyl-1,2,4,5-tetrazine (macrocyclic tetrazine) rendered it unreactive toward trans-cyclooctene. A computational… read more here.
Keywords: tetrazine; electron demand; demand diels; inverse electron ... See more keywords
A Dehydrogenative Inverse Electron Demand Diels-Alder Reaction for the Synthesis of Functionalized Pyranones.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01197
Abstract: An efficient dehydrogenative inverse electron demand Diels-Alder reaction of isopropyl and prenyl benzene derivatives with electron-deficient dienes followed by decarboxylation has been reported for the first time. The much broader substrate scope of dienophiles and… read more here.
Keywords: dehydrogenative inverse; diels alder; inverse electron; demand diels ... See more keywords
Iron-Catalyzed Enantioselective Intramolecular Inverse Electron-Demand Hetero Diels-Alder Reactions: An Access to Bicyclic Dihydropyran Derivatives.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b03752
Abstract: A highly enantioselective iron-catalyzed Intramolecular Inverse Electron-Demand Hetero Diels-Alder (IIEDHDA) reaction is reported. By using a chiral semicorrin ligand in the presence of 2,6-lutidine, good isolated yields and excellent enantioselectivities were observed (up to 96%… read more here.
Keywords: demand hetero; intramolecular inverse; hetero diels; iron catalyzed ... See more keywords
Organocatalytic inverse-electron-demand Diels-Alder reaction between 5-alkenyl thiazolones and β,γ-unsaturated carbonyl compounds.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc00457g
Abstract: An inverse-electron-demand oxa-Diels-Alder reaction of 5-alkenyl thiazolones with β,γ-unsaturated carbonyl compounds enabled by quinine thiourea was studied, which allows the enantioselective synthesis of a broad range of highly functionalized pyranthiazoles bearing three continuous stereocenters. This… read more here.
Keywords: alkenyl thiazolones; diels alder; reaction alkenyl; inverse electron ... See more keywords
Asymmetric inverse-electron-demand 1,3-dipolar cycloadditions of cyclopentadienones and thiophene-1,1-dioxide with C,N-cyclic azomethine imines.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc01103d
Abstract: The normal 1,3-dipolar cycloaddition between the carbonates of 4-hydroxy-2-cyclopentenones and C,N-cyclic azomethine imines can be switched to an inverse-electron-demand version under Pd(0) catalysis, by in situ generation of HOMO-raised η2-Pd(0)-cyclopentadienone complexes. An array of fused… read more here.
Keywords: thiophene dioxide; azomethine imines; inverse electron; cyclic azomethine ... See more keywords
Bioorthogonal micellar nanoreactors for prodrug cancer therapy using an inverse-electron-demand Diels-Alder reaction.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc02121h
Abstract: Block copolymer micelles functionalized with tetrazine groups can act as nanoreactors to activate a trans-cyclooctene-functionalized prodrug for releasing anticancer drugs via a bioorthogonal inverse-electron-demand Diels-Alder (IEDDA) reaction. In addition, the IEDDA reaction can be accelerated… read more here.
Keywords: reaction; diels alder; inverse electron; demand diels ... See more keywords
Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering
Sign Up to like & getrecommendations! Published in 2021 at "Frontiers in Chemistry"
DOI: 10.3389/fchem.2021.654932
Abstract: The inverse electron-demand Diels-Alder (IEDDA or DAinv) reaction is an emerging bioorthogonal ligation reaction that finds application in all areas of chemistry and chemical biology. In this review we highlight its application in metabolic glycoengineering… read more here.
Keywords: diels alder; demand diels; application; inverse electron ... See more keywords