ArticleChemical science2012
A Computational Study of the Origin of Stereoinduction in NHC-Catalyzed Annulation Reactions of α,β-Unsaturated Acyl Azoliums.
Article in Chemical science, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
What it found
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Who cites it
15 citing papers in PubMed.
- Article
- Electrostatic Interactions in Asymmetric Organocatalysis.Accounts of chemical research · 2023Article
- Oxidative N-Heterocyclic Carbene Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Review
- ElectrostaticChemical science · 2022Article
- Tale of the Breslow intermediate, a central player in N-heterocyclic carbene organocatalysis: then and now.Chemical science · 2021Review
- Organocatalytic Name Reactions Enabled by NHCs.Materials (Basel, Switzerland) · 2020Review
- Construction of Dihydropyrido[2,3-The Journal of organic chemistry · 2020Article
- Enantioselective Catalysis of an Anionic Oxy-Cope Rearrangement Enabled by Synergistic Ion Binding.Israel journal of chemistry · 2020Article
- Installation of internal electric fields by non-redox active cations in transition metal complexes.Chemical science · 2019Article
- Proline bulky substituents consecutively act as steric hindrances and directing groups in a Michael/Conia-ene cascade reaction under synergistic catalysis.Chemical science · 2019Article
- A CRSC advances · 2018Article
- Incorporation of redox-inactive cations promotes iron catalyzed aerobic C-H oxidation at mild potentials.Chemical science · 2018Article
- Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.Chemical reviews · 2015Review
- Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine.Chemical science · 2015Article
- Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation byChemical science · 2014Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The origin of stereoselectivity of NHC-catalyzed annulation reactions of ynals and stable enols was studied with Density Functional Theory. The data suggest that the C-C bond formation is the stereo-determining step. Only the deprotonated pathway (containing an oxy anion and overall neutral species) was found to give rise to discrimination of the competing stereoisomers. This is due predominantly to electrostatic repulsion of the β-stabilizing enolate functionality with the π-cloud of the aryl group in the NHC-catalyst.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.