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
IronIII-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins
Sign Up to like & getrecommendations! Published in 2024 at "Chemical Science"
DOI: 10.1039/d4sc00078a
Abstract: The asymmetric catalytic inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with a variety of simple olefins has been accomplished, significantly expanding the applicability of this cyclization to both cyclic hetero-dienes and dienophiles. A new type of strong… read more here.
Keywords: electron demand; demand hetero; inverse electron; hetero diels ... See more keywords
Synthesis of Polyoxygenated 4,5-Diarylpyridazines with Antiproliferative and Antitubulin Activity via Inverse Electron-Demand Diels-Alder Reaction of 1,2,4,5- Tetrazine#
Sign Up to like & getrecommendations! Published in 2024 at "Current Organic Chemistry"
DOI: 10.2174/0113852728314401240613045216
Abstract: The synthesis of a series of multifunctionalized 4,5-diarylpyridazines via inverse electron-demand Diels-Alder reaction between highly oxygenated diarylacetylenes and unsubstituted 1,2,4,5-tetrazine was developed using polyalkoxybenzenes isolated from industrial essential oils as starting material. The reaction proceeded… read more here.
Keywords: reaction; electron demand; demand diels; inverse electron ... See more keywords