ArticleACS catalysis2012
Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.
Article in ACS catalysis, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
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- Asymmetric catalytic [1,3]- or [3,3]-sigmatropic rearrangement of 3-allyloxy-4Chemical science · 2024Article
- Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes.RSC advances · 2023Review
- Oxidative N-Heterocyclic Carbene Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Review
- Hydroxy-directed iridium-catalyzed enantioselective formal β-C(spChemical science · 2022Article
- Alkene Isomerization Revitalizes the Coates-Claisen Rearrangement.Angewandte Chemie (International ed. in English) · 2021Article
- Organocatalytic Name Reactions Enabled by NHCs.Materials (Basel, Switzerland) · 2020Review
- New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.Chemical reviews · 2020Article
- A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation.Chemical science · 2019Article
- Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes.Chemical science · 2018Article
- A CRSC advances · 2018Article
- Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.Nature communications · 2018Article
- Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- 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
- N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals.Synlett : accounts and rapid communications in synthetic organic chemistry · 2015Article
- NHC-Catalyzed Asymmetric Synthesis of Functionalized Succinimides from Enals and α-Ketoamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes.Angewandte Chemie (International ed. in English) · 2012Article
- A Computational Study of the Origin of Stereoinduction in NHC-Catalyzed Annulation Reactions of α,β-Unsaturated Acyl Azoliums.Chemical science · 2012Article
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3 authors.
Funding
Abstract
A combination of a chiral N-heterocyclic carbene catalyst and α,β-unsaturated aldehyde leads to a catalytically generated α,β-unsaturated acyl azolium, which participates in a highly enantioselective annulation to give dihydropyranone products. This full account of our investigations into the scope and mechanism of this reaction reveals the critical role of both the type and substitution pattern of the chiral triazolium precatalyst in inducing and controlling the stereochemistry. In an effort to explain why stable enols such as naphthol, kojic acid, and dicarbonyl are uniquely efficient, we have postulated that this annulation occurs via a Coates-Claisen rearrangement that invokes the formation of a hemiacetal prior to a sigmatropic rearrangement. Detailed kinetic investigations of the catalytic annulation are consistent with this mechanistic postulate.
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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.