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Now showing items 11-20 of 21
Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides
(Georg Thieme Verlag, 2018-06-25)
The functionalization of typically unreactive C(sp3)–H bondsholds great promise for reducing the reliance on existing functionalgroups while improving atom-economy and energy efficiency. As a re-sult, this topic ...
Iron-Catalyzed C(sp3)−H Functionalization of N,N-Dimethylanilines with Isocyanides
(Royal Society of Chemistry, 2018-01-22)
An efficient ligand-free Fe-catalyzed oxidative Ugi-type reaction toward the assembly of α-amino amides and short peptides is described. The reaction proceeds through the α-C(sp3)−H oxidation of N,N-dimethylanilines and ...
Site-Selective Cu-Catalyzed Alkylation of α-Amino Acids and Peptides toward the Assembly of Quaternary Centers
(Wiley, 2018-10-15)
The Cu(I)-catalyzed selective a-alkylation of a-amino acid and peptide derivatives with 2-alkyl-1,3-dioxolanes is reported. This oxidative coupling is distinguished by its site-specificity, high diastereoselectivity, and ...
Cu-Catalyzed Site-Selective C(sp2)–H Radical Trifluoromethylation of Tryptophan Containing Peptides
(ACS Publications, 2020-02-13)
Site-selective functionalization of C–H bonds within a peptide framework poses a challenging task of paramount synthetic relevance. Herein, we report an operationally simple C(sp2)–H trifluoromethylation of tryptophan ...
Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
(American Chemical Society, 2021-09-17)
The selective tagging of amino acids within a peptide framework while using atom-economical C-H counterparts poses an unmet challenge within peptide chemistry. Herein, we report a novel Pd-catalyzed late-stage C-H acylation ...
Ru-Catalyzed C-H Hydroxylation of Tyrosine-Containing Di- and Tripeptides toward the Assembly of L-DOPA Derivatives
(Wiley, 2022-06-21)
[EN] The development of catalytic tools for the late-stage modification of amino acids within a peptide framework is a challenging task of capital importance. Herein, we report a Ru-catalyzed C(sp(2))-H hydroxylation of a ...
On the Mechanism of Cross-Dehydrogenative Couplings between N-Aryl Glycinates and Indoles: A Computational Study
(American Chemical Society, 2020-09-17)
Despite the widespread use of cross-dehydrogenative couplings in modern organic synthesis, mechanistic studies are still rare in the literature and those applied to α-amino carbonyl compounds remain virtually unexplored. ...
Pd-Catalyzed C–H Alkoxycarbonylation of Phenethyl- and Benzylamines with Chloroformates as CO Surrogates
(Wiley, 2021-03-26)
The site‐selective functionalization of C−H bonds within a complex molecule remains a challenging task of capital synthetic importance. Herein, an unprecedented Pd‐catalyzed C(sp2)−H alkoxycarbonylation of phenylalanine ...
Site-Selective C–H Amination of Phenol-Containing Biomolecules
(American Chemical Society, 2023-06)
A C–N bond-forming cross-dehydrogenative coupling of a collection of Tyr-containing peptides and estrogens with heteroarenes is described. This oxidative coupling is distinguished by its scalability, operational simplicity, ...
Palladium-Catalyzed Site-Selective C(sp2)−H Acetoxylation of Tyrosine-Containing Peptides
(Wiley, 2023-02)
A Pd-catalyzed C(sp2)−H acetoxylation of Tyr-containing peptides is described. The method relies on the use of a removable 2-pyridyloxy group as directing group and is distinguished by its reliable scalability and easily ...