ArticleChemical science2020
Strategies for remote enantiocontrol in chiral gold(iii) complexes applied to catalytic enantioselective γ,δ-Diels-Alder reactions.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Predicting Enantioselectivity of Ruthenium-Catalyzed Ketone Hydrogenation with 3D Structure-Based Deep Learning.Journal of the American Chemical Society · 2026Article
- Deconvoluting Nonlinear Catalyst-Substrate Effects in the Intramolecular Dirhodium-Catalyzed C-H Insertion of Donor/Donor Carbenes Using Data Science Tools.ACS catalysis · 2024Article
- A Conformationally Restricted Gold(III) Complex Elicits Antiproliferative Activity in Cancer Cells.Inorganic chemistry · 2023Article
- Enantioselective Catalysis with Pyrrolidinyl Gold(I) Complexes: DFT and NEST Analysis of the Chiral Binding Pocket.JACS Au · 2023Article
- Current Developments ofBiomedicines · 2022Review
- Origin of enantioselectivity reversal in Lewis acid-catalysed Michael additions relying on the same chiral source.Chemical science · 2021Article
- New-Generation Ligand Design for the Gold-Catalyzed Asymmetric Activation of Alkynes.ChemPlusChem · 2021Review
- Recent Developments in Enantioselective Transition Metal Catalysis Featuring Attractive Noncovalent Interactions between Ligand and Substrate.ACS catalysis · 2020Review
- Homogeneous Gold Redox Chemistry: Organometallics, Catalysis, and Beyond.Trends in chemistry · 2020Article
Corrections and comments
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Authors and funding
8 authors.
Funding
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Abstract
The use of chiral square planar gold(iii) complexes to access enantioenriched products has rarely been applied in asymmetric catalysis. In this context, we report a mechanistic and synthetic investigation into the use of N-heterocyclic (NHC) gold(iii) complexes in γ,δ-Diels-Alder reactions of 2,4-dienals with cyclopentadiene. The optimal catalyst bearing a unique 2-chloro-1-naphthyl substituent allowed efficient synthesis of functionally rich carbocycles in good yields, diastereo- and enantioselectivities. Transition state and multivariate linear regression (MLR) analysis of both catalyst and substrate trends using molecular descriptors derived from designer parameter acquisition platforms, reveals attractive non-covalent interactions (NCIs) to be key selectivity determinates. These analyses demonstrate that a putative π-π interaction between the substrate proximal double bond and the catalyst aromatic group is an essential feature for high enantioselectivity.
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Registered trials
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