ArticleNature chemistry2017
Switchable regioselectivity in amine-catalysed asymmetric cycloadditions.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 131 citations in OpenAlex.
- Catalytic Asymmetric Spiroannulation to Access Polycyclic Spiro Enones via Transient Axial-to-Point Chirality Induction and Transfer.Nature communications · 2026Article
- Stereoselective Higher-Order [10+4]- and [10+6] Cycloadditions Between Two Highly Unsaturated and Ambiphilic π-Addends.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Divergent concerted and stepwise cycloadditions via enantioselective cross-conjugated iminium-ion catalysis.Nature communications · 2026Article
- The Diarylprolinol Silyl Ethers: After 20 Years Still Opening New Doors in Asymmetric Catalysis.Angewandte Chemie (International ed. in English) · 2026Review
- Asymmetric formal [1 + 2 + 2]-cycloaddition of diazoamides with enamines and carbonyl compounds.Nature communications · 2025Article
- Switchable organocatalytic enantioselective sulfenocyclization of cyclohexadienes enabling chemodivergent access to chiral bicyclo[m.n.1] ring systems.Nature communications · 2025Article
- Catalyst-controlled regiodivergence and stereodivergence in formal cross-[4+2] cycloadditions: The unique effect of bismuth(III).Science advances · 2025Article
- Highly regioselective synthesis of lactamsRSC advances · 2023Article
- Construction of a synthetic methodology-based library and its application in identifying a GIT/PIX protein-protein interaction inhibitor.Nature communications · 2022Article
- Asymmetric higher-order [10 +Chemical science · 2022Article
- N-Heterocyclic carbene-catalyzed enantioselective hetero-[10 + 2] annulation.Communications chemistry · 2020Article
- New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.Chemical reviews · 2020Article
- Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Ligand and counteranion enabled regiodivergent C-H bond functionalization of naphthols with α-aryl-α-diazoesters.Chemical science · 2019Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Building small-molecule libraries with structural and stereogenic diversity plays an important role in drug discovery. The development of switchable intermolecular cycloaddition reactions from identical substrates in different regioselective fashions would provide an attractive protocol. However, this also represents a challenge in organic chemistry, because it is difficult to control regioselectivity to afford the products exclusively and at the same time achieve high levels of stereoselectivity. Here, we report the diversified cycloadditions of α'-alkylidene-2-cyclopentenones catalysed by cinchona-derived primary amines. An asymmetric γ,β'-regioselective intermolecular [6+2] cycloaddition reaction with 3-olefinic (7-aza)oxindoles is realized through the in situ generation of formal 4-aminofulvenes, while a different β,γ-regioselective [2+2] cycloaddition reaction with maleimides to access fused cyclobutanes is disclosed. In contrast, an intriguing α,γ-regioselective [4+2] cycloaddition reaction is uncovered with the same set of substrates, by employing an unprecedented dual small-molecule catalysis of amines and thiols. All of the cycloaddition reactions exhibit excellent regio- and stereoselectivity, producing a broad spectrum of chiral architectures with high structural diversity and molecular complexity.
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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.