Concept

Cycloaddition

Related publications (89)

Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes

Bicyclic carbocycles containing a high fraction of Csp3 have become highly attractive synthetic targets because of the multiple applications they have found in medicinal chemistry. The formal cycloaddition of bicyclobutanes (BCBs) with two- or three-atom p ...

Royal Soc Chemistry2024

Head‐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 ...

2023

Photochemical [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 ...

2023

Activation of aminocyclopropanes via radical intermediates

Jérôme Waser, Mingming Wang

Aminocyclopropanes are versatile building blocks for accessing high value-added nitrogen-containing products. To control ring-opening promoted by ring strain, the Lewis acid activation of donor-acceptor substituted systems is now well established. Over the ...

2022

Visible light activated BINOL-derived chiroptical switches based on boron integrated hydrazone complexes

Lukas Pfeifer

Chiral optical switches, which use light to control chirality in a reversible manner, offer unique properties and fascinating prospects in the areas of molecular switching and responsive systems, new photochromic materials and molecular data processing and ...

ROYAL SOC CHEMISTRY2022

Development 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 ...

EPFL2021

Alkynyl triazenes enable divergent syntheses of 2-pyrones

Kay Severin, Nicolai Cramer, Carl Thomas Bormann, Jin Fay Tan

The 2-pyrone motif occurs frequently in bioactive natural products and is appreciated as synthetic intermediates. However, only few methods allow for diversifying functional group modifications on this relevant heterocycle. The distinct properties of 1-alk ...

2021

Isolation and characterization of diazoolefins

Rosario Scopelliti, Kay Severin, Farzaneh Fadaei Tirani, Zhaowen Dong, Paul Varava

Diazoolefins tend to be highly reactive compounds that rapidly lose dinitrogen. So far, most experimental evidence for diazoolefins is indirect, via trapping experiments. Here we show that diazoolefins are observed to form in reactions of N-heterocyclic ol ...

2021

Copper-Catalyzed 1,2-Methoxy Methoxycarbonylation of Alkenes with Methyl Formate and Synthetic Studies Towards the Total Synthesis of Koumine, Voacafricine A and Voacafricine B

Balázs Budai

The development of an unusual oxidative alkene difunctionalization using methyl formate and syn-thetic studies towards alkaloid natural products provide the basis of the thesis. The first chapter details the development of a method that forges methoxycarbo ...

EPFL2020

Low‐Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands

Rosario Scopelliti, Jérôme Waser, Farzaneh Fadaei Tirani, Matthew Wodrich, Durga Prasada Rao Hari, Guillaume Dominique Pisella, Artem Tsymbal

The intramolecular [4+2] cycloaddition between arenes and allenes first reported by Himbert gives rapid access to rigid polycyclic scaffolds. Herein, we report a one‐pot oxyalkynylation/cycloaddition reaction proceeding under mild conditions (23–90 °C) and ...

2020

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