ArticleNature communications2016
Computational ligand design in enantio- and diastereoselective ynamide [5+2] cycloisomerization.
Article in Nature communications, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- An Asymmetric Approach toward theOrganic letters · 2025Article
- Mathematical Framework to Identify Optimal Molecule Based on Virtual Ligand Strategy.Journal of chemical information and modeling · 2025Article
- Stereo-Differentiating Asymmetric Rh(I)-Catalyzed Pauson-Khand Reaction: A DFT-Informed Approach to Thapsigargin Stereoisomers.Journal of the American Chemical Society · 2025Article
- Data-driven discovery of active phosphine ligand space for cross-coupling reactions.Chemical science · 2024Article
- Ir/Zn-cocatalyzed chemo- and atroposelective [2+2+2] cycloaddition for construction of C─N axially chiral indoles and pyrroles.Science advances · 2023Article
- Sequencing palladium-catalyzed cycloisomerization cascades in a synthesis of the gelsemine core.Chemical science · 2023Article
- Computational molecular refinement to enhance enantioselectivity by reinforcing hydrogen bonding interactions in major reaction pathway.Chemical science · 2023Article
- Noncovalent CH-π and π-π Interactions in Phosphoramidite Palladium(II) Complexes with Strong Conformational Preference.Angewandte Chemie (International ed. in English) · 2021Article
- Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.Chemical reviews · 2021Article
- Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications.Chemical Society reviews · 2020Article
- Retooling Asymmetric Conjugate Additions for Sterically Demanding Substrates with an Iterative Data-Driven Approach.ACS catalysis · 2019Article
- Mechanistically Guided Predictive Models for Ligand and Initiator Effects in Copper-Catalyzed Atom Transfer Radical Polymerization (Cu-ATRP).Journal of the American Chemical Society · 2019Article
- Synthesis of poly-functionalized benzofuransRSC advances · 2019Article
- Mechanistically Guided Design of Ligands That Significantly Improve the Efficiency of CuH-Catalyzed Hydroamination Reactions.Journal of the American Chemical Society · 2018Article
- Computational design of high-performance ligand for enantioselective Markovnikov hydroboration of aliphatic terminal alkenes.Nature communications · 2018Article
- Formation of quaternary centres by copper catalysed asymmetric conjugate addition to β-substituted cyclopentenones with the aid of a quantitative structure-selectivity relationship.Chemical science · 2018Article
- Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis.Chemical science · 2017Article
- Ligand-Substrate Dispersion Facilitates the Copper-Catalyzed Hydroamination of Unactivated Olefins.Journal of the American Chemical Society · 2017Article
- Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions.Organic letters · 2017Article
- Correlating Reactivity and Selectivity to Cyclopentadienyl Ligand Properties in Rh(III)-Catalyzed C-H Activation Reactions: An Experimental and Computational Study.Journal of the American Chemical Society · 2017Article
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5 authors.
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Abstract
Transition metals can catalyse the stereoselective synthesis of cyclic organic molecules in a highly atom-efficient process called cycloisomerization. Many diastereoselective (substrate stereocontrol), and enantioselective (catalyst stereocontrol) cycloisomerizations have been developed. However, asymmetric cycloisomerizations where a chiral catalyst specifies the stereochemical outcome of the cyclization of a single enantiomer substrate--regardless of its inherent preference--are unknown. Here we show how a combined theoretical and experimental approach enables the design of a highly reactive rhodium catalyst for the stereoselective cycloisomerization of ynamide-vinylcyclopropanes to [5.3.0]-azabicycles. We first establish highly diastereoselective cycloisomerizations using an achiral catalyst, and then explore phosphoramidite-complexed rhodium catalysts in the enantioselective variant, where theoretical investigations uncover an unexpected reaction pathway in which the electronic structure of the phosphoramidite dramatically influences reaction rate and enantioselectivity. A marked enhancement of both is observed using the optimal theory-designed ligand, which enables double stereodifferentiating cycloisomerizations in both matched and mismatched catalyst-substrate settings.
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