ArticleJournal of the American Chemical Society2015
Ligand-enabled β-C-H arylation of α-amino acids using a simple and practical auxiliary.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
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Who cites it
41 citing papers in PubMed, 166 citations in OpenAlex.
- Pd(II)-Catalyzed Strategies for the β-Arylation of α-Amino Acids: An Overview.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Reprogramming RiPP scaffolds through skeletal editing unlocks chemical space.Chemical science · 2026Article
- Synthetic Applications of Hydroxamic Acids and Their Derivatives in Organic Chemistry.ACS organic & inorganic Au · 2026Review
- Successive diastereoselective C(spRSC advances · 2025Article
- Direct asymmetric synthesis of β-branched aromatic α-amino acids using engineered phenylalanine ammonia lyases.Nature communications · 2024Article
- A directed enolization strategy enables by-product-free construction of contiguous stereocentres en route to complex amino acids.Nature chemistry · 2024Article
- Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C-H activation.Chemical science · 2023Article
- β- and γ-C(spAngewandte Chemie (International ed. in English) · 2023Article
- Iridium-Catalyzed Borylation of 6-Fluoroquinolines: Access to 6-Fluoroquinolones.The Journal of organic chemistry · 2022Article
- Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(spChemical reviews · 2021Review
- Stereodivergent entry to β-branched β-trifluoromethyl α-amino acid derivatives by sequential catalytic asymmetric reactions.Chemical science · 2021Article
- Stereoselective Synthesis of β-Branched Aromatic α-Amino Acids by Biocatalytic Dynamic Kinetic Resolution*.Angewandte Chemie (International ed. in English) · 2021Article
- Chemodivergent manganese-catalyzed C-H activation: modular synthesis of fluorogenic probes.Nature communications · 2021Article
- Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C-H activation.Chemical science · 2021Review
- Late-stage stitching enabled by manganese-catalyzed C─H activation: Peptide ligation and access to cyclopeptides.Science advances · 2021Article
- Tryptophan Analogues with Fixed Side-Chain Orientation: Expanding the Scope.Chembiochem : a European journal of chemical biology · 2021Article
- Late-stage C(spChemical science · 2020Article
- Side Chain Orientation of Tryptophan Analogues Determines Agonism and Inverse Agonism in Short Ghrelin Peptides.ChemMedChem · 2019Article
- Total Synthesis and Stereochemical Assignment of Streptide.Journal of the American Chemical Society · 2019Article
- Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes.Journal of the American Chemical Society · 2019Article
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Authors and funding
13 authors at 2 institutions in 1 country.
Funding
Abstract
Pd-catalyzed β-C-H functionalizations of carboxylic acid derivatives using an auxiliary as a directing group have been extensively explored in the past decade. In comparison to the most widely used auxiliaries in asymmetric synthesis, the simplicity and practicality of the auxiliaries developed for C-H activation remains to be improved. We previously developed a simple N-methoxyamide auxiliary to direct β-C-H activation, albeit this system was not compatible with carboxylic acids containing α-hydrogen atoms. Herein we report the development of a pyridine-type ligand that overcomes this limitation of the N-methoxyamide auxiliary, leading to a significant improvement of β-arylation of carboxylic acid derivatives, especially α-amino acids. The arylation using this practical auxiliary is applied to the gram-scale syntheses of unnatural amino acids, bioactive molecules, and chiral bis(oxazoline) ligands.
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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.