ArticleNature chemistry2015
Switchable selectivity in an NHC-catalysed dearomatizing annulation reaction.
Article in Nature chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Review
- Catalytic asymmetric synthesis of (N, N)- spiroketal via Pd-catalyzed enantioconvergent aminocarbonylation and dearomative nucleophilic aza-addition.Nature communications · 2025Article
- Article
- Regiodivergent Nucleophilic Fluorination under Hydrogen Bonding Catalysis: A Computational and Experimental Study.Journal of the American Chemical Society · 2023Article
- Ir and NHC Dual Chiral Synergetic Catalysis: Mechanism and Stereoselectivity in γ-Butyrolactone Formation.Journal of the American Chemical Society · 2022Article
- The Role of the Fused Ring in Bicyclic Triazolium Organocatalysts: Kinetic, X-ray, and DFT Insights.The Journal of organic chemistry · 2022Article
- The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products.Organic chemistry frontiers : an international journal of organic chemistry · 2020Article
- Regio- and diastereoselective dearomatizations ofChemical science · 2019Article
- Ligand and counteranion enabled regiodivergent C-H bond functionalization of naphthols with α-aryl-α-diazoesters.Chemical science · 2019Article
- Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions.Nature communications · 2019Article
- Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.Organic & biomolecular chemistry · 2019Review
- Mechanism and stereoselectivity in NHC-catalyzed β-functionalization of saturated carboxylic ester.RSC advances · 2019Article
- A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation.Chemical science · 2019Article
- Copper-Catalyzed Heteroarylboration of 1,3-Dienes with 3-Bromopyridines: A cine Substitution.Angewandte Chemie (International ed. in English) · 2018Article
- A CRSC advances · 2018Article
- Switchable regioselectivity in amine-catalysed asymmetric cycloadditions.Nature chemistry · 2017Article
- Structurally Divergent Lithium Catalyzed Friedel-Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Palladium-Catalyzed Oxidative Carbocyclization-Borylation of Enallenes to Cyclobutenes.Angewandte Chemie (International ed. in English) · 2016Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of general catalytic methods for the regio- and stereoselective construction of chiral N-heterocycles in a diversity-oriented fashion remains a formidable challenge in organic synthesis. N-heterocyclic carbene (NHC) catalysis has been shown to produce a variety of outcomes, but control of the reactivity has rarely been demonstrated. Here we report a switchable catalytic activation of enals with aromatic azomethine imines that provides high selectivity using NHC organocatalysts. The original selectivity corresponds to the acidity of the base used in the reaction. The catalytically generated chiral homoenolate or enol intermediate undergoes enantioselective annulation with electrophiles such as N-iminoquinolinium ylides, N-iminoisoquinolinium ylides and β-N-iminocarboline ylides. The good-to-high overall yields, high regioselectivities and excellent enantioselectivities observed are controlled by the catalyst and reaction conditions.
Identifiers
26391085What OpenQuestion holds
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.