Concept
1,3-Dipolar cycloaddition
Related publications (124)
Functionalization of harmonic nanoparticles for drug release and multimodal imaging applications
Cancer is among the leading causes of death worldwide, and as knowledge of the disease continues to grow there is an increasing interest towards precision medicine: more specifically towards the theranostics field, i.e the development of targeted molecular ...
EPFL2024Novel Alkynylation Methods through the Combination of Hypervalent Iodine Reagents and Alkynyl-trifluoroborate Salts
The alkyne motif is a versatile functional group often encountered in organic chemistry. It can be involved in various transformations such as the alkyne-azide cycloaddition and has found widespread application in medicinal chemistry, chemical biology and ...
EPFL2024Head‐to‐Tail Dimerization of N‐Heterocyclic Diazoolefins
Rosario Scopelliti, Kay Severin, Farzaneh Fadaei Tirani, Andrzej Sienkiewicz, Tak Hin Wong, Zhaowen Dong, Paul Varava, Anastasia Gitlina, Wolfram Feuerstein
The head-to-tail dimerization of N-heterocyclic diazoolefins is described. The products of these formal (3+3) cycloaddition reactions are strongly reducing quinoidal tetrazines. Oxidation of the tetrazines occurs in a stepwise fashion, and we were able to ...
2023Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B
Qian Wang, Jieping Zhu, Rémi Hugo Lavernhe
Transition-metal-catalyzed [4+2] heteroannulation of alpha,beta-unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis of pyridines. It nevertheless lacks regioselectivity when unsymmetrically su ...
WILEY-V C H VERLAG GMBH2023Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A
The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...
EPFL2023Synthesis and application of bifunctional hypervalent iodine reagents for peptide modification.
Protein-protein interactions (PPIs) are responsible for regulating many biological processes in human bodies. PPIs often have a large binding site and often interact through an alpha helical segment. Therefore, the inhibition of PPIs can be difficult using ...
EPFL2023Photochemical [2+2] Cycloaddition of Alkynyl Boronates
Jérôme Waser, Oleksandr Liashuk
A photochemical [2+2] cycloaddition of alkynyl boronates and maleimides is reported. The developed protocol provided 35–70 % yield of maleimide-derived cyclobutenyl boronates and demonstrated wide compatibility with various functional groups. The synthetic ...
2023N-Terminal Selective C-H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification
Jérôme Waser, Raphaël Michel Henri Simonet-Davin, Emmanuelle Madeline Dominique Allouche
A methodology for the C-H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at th ...
WILEY-V C H VERLAG GMBH2022Development of remote C-H bond functionalization of redox-active alcohol derivatives and oxidative transformations under photoredox catalysis
Alexandre Julien Florent Leclair
The development of radical-based remote C(sp3)-H functionalizations of redox-active alcohol derivatives, oxidative cycloaddition and rearrangement transformations under visible light photocatalysis constitute the basis of this thesis.The first chapter desc ...
EPFL2021Asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces
Harald Brune, Roland Hany, Roland Widmer, Michael Bauer, Samuel Thomas Stolz
Achieving fundamental understanding of enantioselective heterogeneous synthesis is marred by the permanent presence of multitudinous arrangements of catalytically active sites in real catalysts. In this study, we address this issue by using structurally co ...
NATURE RESEARCH2021