ArticleiScience2020
Two Catalytic Annulation Modes via Cu-Allenylidenes with Sulfur Ylides that Are Dominated by the Presence or Absence of Trifluoromethyl Substituents.
Article in iScience, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Cooperative Dual Organocatalytic Asymmetric Decarboxylative [4 + 3] Annulations with Benzoxazinanones.Precision chemistry · 2023Article
- Construction of poly-N-heterocyclic scaffolds via the controlled reactivity of Cu-allenylidene intermediates.Communications chemistry · 2021Article
- Synthesis of Tetra-Substituted Trifluoromethyl-3,1-Benzoxazines by Transition-Metal-Catalyzed Decarboxylative Cyclization of N-Benzoyl Benzoxazinones.ChemistryOpen · 2021Article
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Authors and funding
4 authors.
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No grant is acknowledged in the PubMed record.
Abstract
We disclose the Cu-catalyzed enantioselective synthesis of 3-methyl-3-propargyl-indolines, which contain a quaternary stereogenic carbon center, via the decarboxylative [4 + 1] annulation of 4-methyl-4-propargyl-benzoxazinanones with variety of sulfur ylides. The reaction proceeds predominantly through a γ-attack at the Cu-allenylidene intermediates by sulfur ylides to provide the corresponding indolines in good yield and high enantioselectivity (up to 91% ee). In contrast, the reaction of 4-trifluoromethyl-4-propargyl-benzoxazinanones with sulfur ylides delivers 3-trifluoromethyl-2-functionalized indoles in good to high yield via an unexpected α-attack at the Cu-allenylidene intermediates. Control over the α/γ-attack at the Cu-allenylidene intermediates by the same interceptors was achieved for the first time by the use of trifluoromethyl substituents.
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