Diels–Alder Cycloadditions of Masked <i>o</i>-Benzoquinones with Alkenes

Georgopanou, Effie; Martini, Katerina-Irene; Pantazis, Panagiotis; Pelagias, Paulos; Voulgari, Penelope; Hadjiarapoglou, Lazaros P.

doi:10.1021/acs.joc.5b01755

Cited by 12 publications

(2 citation statements)

References 53 publications

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“…The use of vinyl sulfides as dienophiles for Diels-Alder reactions (both in full carbon and heteroatomic versions) is conventional and does not require special discussion. As a demonstration of the great importance of vinyl sulfides in this field, there are several recent examples of enantioselective syntheses, [75][76][77][78] the assembly of complex natural scaffolds, [79] and photochemically induced reactions. [80] A similar situation is observed in the case of [2 + 3] dipolar cycloaddition [81][82][83] and [2+2] cycloaddition.…”

Section: S-activated Alkenes and Dienesmentioning

confidence: 99%

Sulfur in Waste‐Free Sustainable Synthesis: Advancing Carbon–Carbon Coupling Techniques

Shlapakov,

Kobelev,

Burykina

et al. 2024

Angewandte Chemie

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This review explores the pivotal role of sulfur in advancing sustainable carbon‐carbon (C–C) coupling reactions. The unique electronic properties of sulfur, as a soft Lewis base with significant mesomeric effect make it an excellent candidate for initiating radical transformations, directing C–H‐activation, and facilitating cycloaddition and C–S bond dissociation reactions. These attributes are crucial for developing waste‐free methodologies in green chemistry. Our mini‐review is focused on existing sulfur‐directed C–C coupling techniques, emphasizing their sustainability and comparing state‐of‐the‐art methods with traditional approaches. The review highlights the importance of this research in addressing current challenges in organic synthesis and catalysis. The innovative use of sulfur in photocatalytic, electrochemical and metal‐catalyzed processes not only exemplifies significant advancements in the field but also opens new avenues for environmentally friendly chemical processes. By focusing on atom economy and waste minimization, the analysis provides broad appeal and potential for future developments in sustainable organic chemistry.

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Section: S-activated Alkenes and Dienesmentioning

confidence: 99%

Sulfur in Waste‐Free Sustainable Synthesis: Advancing Carbon–Carbon Coupling Techniques

Shlapakov,

Kobelev,

Burykina

et al. 2024

Angewandte Chemie

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“…The inter‐ and intramolecular reactions of styrenes diversely undergo [2+2] cycloadditions,, and [4+2] cycloadditions as dienophile components , . Limited intermolecular [4+2] cycloadditions of styrenes as dienes were also reported .…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Cyclization of 3,3‐Diarylpropenylamides of Electron‐Deficient Alkenes: Stereoselective Synthesis of Functionalized Hexahydrobenzo[f]isoindoles

Sugiura

Yamazaki

2018

Eur J Org Chem

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Intramolecular Diels–Alder reactions of various 3,3‐diarylpropenylamides of electron‐deficient alkenes to give hexahydrobenzo[f]isoindoles were investigated. Reaction of 1,1,2‐ethenetricarboxylic acid 1,1‐diethyl ester with 3,3‐diaryl‐2‐propen‐1‐amines under the amide formation conditions gave the tricyclic compounds in sequential processes involving intramolecular Diels–Alder reaction. The reaction gave cis‐ and trans‐fused tricyclic compounds selectively, depending on the substituents on the benzene ring, reaction temperature and solvent. In the reaction with dissymmetrically substituted 3,3‐diaryl‐2‐propen‐1‐amines, trans‐substituted aryl group reacted mainly as a styrene component. Amides of electron‐deficient alkenic carboxylic acids such as fumarate do not undergo cyclization at room temperature sequentially and the reaction on heating gave trans‐fused hexahydrobenzo[f]isoindoles. The origin of the observed stereoselectivity has been examined by the DFT calculations.

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Addition Reactions: Cycloaddition

Dennis¹

2019

Organic Reaction Mechanisms Series

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Diels–Alder Cycloadditions of Masked o-Benzoquinones with Alkenes

Cited by 12 publications

References 53 publications

Sulfur in Waste‐Free Sustainable Synthesis: Advancing Carbon–Carbon Coupling Techniques

Sulfur in Waste‐Free Sustainable Synthesis: Advancing Carbon–Carbon Coupling Techniques

Intramolecular Cyclization of 3,3‐Diarylpropenylamides of Electron‐Deficient Alkenes: Stereoselective Synthesis of Functionalized Hexahydrobenzo[f]isoindoles

Addition Reactions: Cycloaddition

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