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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 ...
Ni- and Fe-Based Cross-Coupling Reactions. Editorial
(Springer, 2016-09-26)
The series Topics in Current Chemistry Collections presents critical reviews from the journal Topics in Current Chemistry organized in topical volumes. The goal of this thematic volume is to give the non-specialist reader, ...
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, ...