Enamides: valuable organic substrates

Carbery, David R.

doi:10.1039/b809319a

Cited by 310 publications

(103 citation statements)

References 66 publications

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“…Many of these new rearrangements make use of the vinyl urea functional group-a class of acylated enamines [61] that has rarely been exploited until now. The vinyl ureas may be made from their parent imines, or by rearrangement of the isomeric allylic ureas.…”

Section: Electrophilicity Of Aryl and Vinyl Ureasmentioning

confidence: 99%

The Urea Renaissance

2011

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Over the last decade the use of urea derivatives as useful reagents, catalysts, and structural features in organic chemistry has increased rapidly. They now find utility as hydrogen-bond donors in organocatalysts and anion transporters, as important scaffolds in supramolecular chemistry, as lithiation directors, amination substrates, and promoters of metalation, and as substrates for novel rearrangement reactions. Highlighted herein is the remarkably rapid and recent development of the chemistry of ureas, which for many years had been considered unreactive, intractable, and of little value.

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Section: Electrophilicity Of Aryl and Vinyl Ureasmentioning

confidence: 99%

The Urea Renaissance

2011

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“…Die katalytische asymmetrische Diaminierung von konjugierten Dienen und Trienen [54] Viele dieser neuen Umlagerungen nutzen die funktionelle Gruppe des Vinylharnstoffs -eine Klasse von acylierten Enaminen, [61] die bisher nur wenig genutzt wurde. Die Vinylharnstoffe kçnnen aus den entsprechenden Iminen oder durch Umlagerung der isomeren Allylharnstoffe hergestellt werden.…”

Section: Palladium-dirigierte Aminierung Mit Harnstoffenunclassified

Die Harnstoff‐Renaissance

Volz

Clayden

2011

Angewandte Chemie

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Im letzten Jahrzehnt hat die Verwendung von Harnstoffderivaten als wertvolle Reagentien, Katalysatoren und Struktureinheiten in der organischen Chemie rasch zugenommen. Sie finden nun Verwendung als Wasserstoffbrückendonoren in Organokatalysatoren und Anionentransportern, als wichtige Struktureinheit in der supramolekularen Chemie, für die Steuerung von Lithiierungen, als Aminierungssubstrate, für die Vermittlung von Metallierungen und als Substrate für neuartige Umlagerungen. In diesem Aufsatz wird die bemerkenswert rasche aktuelle Entwicklung der Chemie des Harnstoffs hervorgehoben, der für viele Jahre als unreaktiv, schwer zu handhaben und vergleichsweise wertlos betrachtet wurde.

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“…Polarized alkenes, such as enol ethers 103,104 and enamides, 105–107 have been widely applied in [3+2]-dipolar cycloaddition reactions. As illustrated in Scheme 9, the resonance contributing structure of catalytically generated metallo-enolcarbenes provides an ideal dipolar three-carbon scaffold for [3+2]-cycloaddition reactions with polarized alkenes.…”

Section: Mecc Reactions Of Enoldiazo Compoundsmentioning

confidence: 99%

Cycloaddition reactions of enoldiazo compounds

et al. 2017

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Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+n]-cycloadditions (n = 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+n]-cycloadditions (n = 1–5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+n]-cycloadditions (n = 3, 4) by donor–acceptor cyclopropenes generated in situ from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium(II) and the emergence of copper(I) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community.

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Enamides: valuable organic substrates

Cited by 310 publications

References 66 publications

The Urea Renaissance

The Urea Renaissance

Die Harnstoff‐Renaissance

Cycloaddition reactions of enoldiazo compounds

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