New mechanistic interpretations for nitrone reactivity

Merino, Pedro; Tejero, Tomás; Delso, J. Ignacio; Matute, Rosa

doi:10.1039/c7ob00429j

Cited by 43 publications

(30 citation statements)

References 108 publications

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“…A similar asynchronicity was observed for all TSxSi transition structures. In all cases, the latter bond to be formed corresponded to the C‐O bond in agreement with a classical pericyclic reaction rather than a more polar one‐step‐two stage process …”

Section: Resultssupporting

confidence: 62%

Experimental and Computational Studies on the 1,3‐Dipolar Cycloaddition between Enantiomerically Pure 2,3‐Dihydrothiazoles and Nitrones

et al. 2019

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The diastereoselective 1,3‐dipolar cycloaddition between nitrones and enantiomerically pure 2,3‐dihydrothiazoles derived from L‐cysteine, with different oxidation states at the sulfur atom has been studied experimentally and computationally. The reaction takes place with complete regioselectivity and diastereofacial selectivity. On the other hand, the exo/endo selectivity showed a clear dependence of the oxidation state at the sulfur atom. The computational calculations agree with the experimental findings.

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Section: Resultssupporting

confidence: 62%

Experimental and Computational Studies on the 1,3‐Dipolar Cycloaddition between Enantiomerically Pure 2,3‐Dihydrothiazoles and Nitrones

et al. 2019

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“…Biomass‐derived furan is a highly crucial synthetic tool because of its low aromaticity . It does not only can serve as masked alkenes, enol ethers, 1,4‐diketones, and carboxylic acids, but also usually can allow for facile recyclization reactions into different carbo and heterocycles . However, to the best of our knowledge, a direct transformation from furans to thioesters has never been achieved in organic synthesis.…”

Section: Methodsmentioning

confidence: 99%

Furfuryl Cation Induced Three‐Component Reaction to Synthesize Triazole‐Substituted Thioesters

Zhao

Xing

et al. 2020

Eur J Org Chem

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A furfuryl cation induced three‐component thioesterification reaction between thiols, 5‐bromo‐2‐furylcarbinols and azides is reported. This metal‐free method relies on the acetyl chloride/HFIP‐mediated cascade formal [3+2] cycloaddition/ring‐opening/thioesterification, which allows the efficient construction of a series of complex triazole‐thioesters linked with an (Z)‐olefin. Selenols are also suitable for this strategy. Further derivatization of thioesters highlighted the potential utility of our method.

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“…In particular, the reaction between nitrones and isocyanates was described making use of noncovalent interactions (NCI) and ELF studies while the evolution of ELF along the reaction was analyzed for the [3 + 2] cycloaddition reactions of nitrones with electron‐deficient ethylenes or ketenes, as well as for the [3 + 2] cycloaddition reactions of C,N Dialkyl nitrones with ethylene derivatives . A review on the analysis of the ELF evolution associated to nitrones reactivity has been presented recently, highlighting the sequential way of formation of the bonds . Similar reactions have been studied for explicitly evaluating the synchronicity by using ELF …”

Section: Introductionmentioning

confidence: 99%

How effectively bonding evolution theory retrieves and visualizes curly arrows: The cycloaddition reaction of cyclic nitrones

Adjieufack

Bake

Mbadcam

et al. 2019

Int J of Quantum Chemistry

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In the present work, the electron density flows involved throughout the progress of the four reaction pathways associated with the intramolecular [3 + 2] cycloaddition of cyclic nitrones Z-1 and E-1 are analyzed using the bonding evolution theory. The present study highlights the nonconcerted nature of the processes, which can be described as taking place in several stages. The first stage consists in the depopulation of the initial C N and C C double bonds to render the N lone pair and the corresponding C N and C C single bonds, and these electronic flows initiate the reactions. The C C and C O sigma bond formations take place later on, once the transition states have been overcome. Along the bridged pathways, the C C bond formation process precedes the O C bond formation event, although, along the fused paths, the O C bond formation process occurs first and the formation of the C C bond is the last electronic flow to take place. Finally, curly arrow representations accounting for the timing of the electron flows are obtained from the bonding evolution theory results. K E Y W O R D S bonding evolution theory, curly arrows, cyclic nitrones, intramolecular [3 + 2]cycloaddition

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New mechanistic interpretations for nitrone reactivity

Cited by 43 publications

References 108 publications

Experimental and Computational Studies on the 1,3‐Dipolar Cycloaddition between Enantiomerically Pure 2,3‐Dihydrothiazoles and Nitrones

Experimental and Computational Studies on the 1,3‐Dipolar Cycloaddition between Enantiomerically Pure 2,3‐Dihydrothiazoles and Nitrones

Furfuryl Cation Induced Three‐Component Reaction to Synthesize Triazole‐Substituted Thioesters

How effectively bonding evolution theory retrieves and visualizes curly arrows: The cycloaddition reaction of cyclic nitrones

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