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Concept

Intramolecular reaction

Related publications (12)

Photocatalyzed [2σ + 2σ] and [2σ + 2π] Cycloadditions for the Synthesis of Bicyclo[3.1.1]heptanes and 5- or 6-Membered Carbocycles

Jérôme Waser, Matthew Wodrich, Vu Trung Tin Nguyen

We report the use of photocatalysis for the homolytic ring-opening of carbonyl cyclopropanes. In contrast to previous studies, our approach does not require a metal cocatalyst or a strong reductant. The carbonyl cyclopropanes can be employed for both [2σ + ...

2023

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Bastian Antoine Rodolphe Claude Muriel

Amino alcohols, cyclopropanes and nitriles are privileged structural motifs found in the scaffold of natural products and bioactive compounds. In addition, they are versatile building blocks in organic chemistry. The development of new and increasingly eff ...

EPFL2021

Copper-catalyzed transformations of carboradicals generated by electrochemical and photochemical methods: oxidative amination and polyfluoroarylation

Xiangli Yi

Organic radicals are highly active species that can undergo various transformations. Electrochemistry and photochemistry are efficient methods for the generation of these species of high energy, through single electron transfer processes under mild conditi ...

EPFL2021

Towards the Sarpagine-Ajmaline-Macroline Family of Indole Alkaloids: Enantioselective Synthesis of an N-Demethyl Alstolactone Diastereomer

Jieping Zhu, Qian Wang, Dylan Jean Robert Dagoneau

the strategy involving the use of functionalized tetrahydro-6H-cycloocta[b]indol-6-one is reported as a key intermediate for synthesis of members of the sarpagine-ajmaline-macroline family of monoterpene indole alkaloids. The desired tricycle was synthesiz ...

WILEY-V C H VERLAG GMBH2020

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

EPFL2020

Catalytic C-C Bond Activations via Oxidative Addition to Transition Metals

Nicolai Cramer, Laetitia Marie Mélanie Souillart

Selective cleavages of carbon-carbon bonds catalyzed by transition-metal complexes have been shown to be increasingly versatile tools for organic synthesis allowing for complementary synthetic strategies. Numerous examples of transition-metal catalyzed C-C ...

Amer Chemical Soc2015

Catalytic Formal Homo-Nazarov Reaction and Other Cyclizations of Cyclopropanes : from Methodology to Total Synthesis

Filippo De Simone

The increasing progress in medicinal chemistry and chemical biology requires more versatile synthetic strategies for the generation of libraries of active compounds and theirs analogues. A wide range of biologically active natural and synthetic compounds c ...

EPFL2012

Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes

Jérôme Waser, Fides Benfatti, Tanguy Jean Daniel Saget, Filippo De Simone

The Nazarov cyclization of divinyl ketones gives access to cyclopentenones. Replacing one of the vinyl groups by a cyclopropane leads to a formal homo-Nazarov process for the synthesis of cyclohexenones. In contrast to the Nazarov reaction, the cyclization ...

2011

[(Methylcarbamothioyl)disulfanyl]methyl N-methylcarbamodithioate

The title compound, C5H10N2S5, was unintentionally obtained as the product of an attempted synthesis of a methyl-carbamodithioic acid using methylamine and carbon disulfide. In the molecule, two dithiocarbamate groups are bridged by a -CH2S- unit. The C-S- ...

2010

Cyclization of Cyclopropyl Carbonyls and the Homo-Nazarov Reaction

Jérôme Waser, Filippo De Simone

Ring strain confers to the cyclopropane ring an exceptional reactivity. Nevertheless, activation of the cyclopropane ring is usually needed to allow ring-opening reactions under mild conditions. The introduction of one or several carbonyl functionalities o ...

2009

Empirical Corrections to Density Functional Theory Highlight the Importance of Nonbonded Intramolecular Interactions in Alkanes

Anne-Clémence Corminboeuf, Matthew Wodrich, Daniel Filipe Dos Santos Alves Jana

Energies of alkanes computed with many popular and even newer density functionals are flawed by systematic errors, which become considerable with larger molecules. The same energies, however, are well described by post-Hartree-Fock methods. Similar DFT sho ...

2008

Investigations of Diels-Alder reactions in ionic liquids

Ana Vidis

Room temperature ionic liquids comprise an unique class of solvent composed of organic and inorganic-based ions that are molten under ambient conditions. They are characterised by high solvent polarity and low vapour pressure, and can be tailored to have s ...

EPFL2007