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Asymmetric Construction of alpha,alpha-Disubstituted Piperazinones Enabled by Benzilic Amide Rearrangement

Publications associées (37)

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Development of New Strategies of Umpolung with Cyclic Hypervalent Iodine Reagents

Paola Caramenti

Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from s ...

EPFL2019

Recent Advances in Catalytic Enantioselective Rearrangement

Qian Wang, Jieping Zhu, Hua Wu

Among the fundamental chemical transformations in organic synthesis, rearrangement has been recognized as powerful and reliable reactions for the construction of carbon-carbon or carbon-heteroatom bonds. Benefiting from the advance of the novel catalytic s ...

2019

Design and validation of bioorthogonal probes for cellular disease models

Pier Luca D'Alessandro

Well-validated chemical probes enable testing of biological hypotheses, investigation of target tractability and translatability to the clinical phase. Consequently, these important tool compounds play a key role in the drug discovery process. Moreover, th ...

EPFL2019

Manganese-mediated reductive amidation of esters with nitroarenes

Xile Hu, Peng Wang, Chi Wai Cheung, Ning Shen

Amides are ubiquitous molecules in nature and in synthetic chemistry. Here we report a convenient and efficient method to synthesize N-aryl amides via amidation of esters with nitroarenes. In the presence of manganese metal, this amidation proceeded smooth ...

ROYAL SOC CHEMISTRY2019

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Controlling the cis C20/C21 relative stereochemistry remains an unsolved issue in the synthesis of eburnane-type indole alkaloids. Provided herein is a simple solution to this problem by developing a unified and diastereoselective synthesis of four represe ...

2019

Decarboxylative C(sp3 )−O Cross-Coupling

Xile Hu, Runze Mao, Jonathan Balon

Alkyl aryl ethers are an important class of compounds in medicinal and agricultural chemistry. Catalytic C(sp3)−O cross‐coupling of alkyl electrophiles with phenols is an unexplored disconnection strategy to the synthesis of alkyl aryl ethers, with the pot ...

2018

Indole Alkaloids, Macrocycles and Heterocycles

Cyril Piemontesi

An enantioselective total synthesis of (-)-terengganensine A, a heptacyclic monoterpene indole alkaloid, was performed. A short sequence allowed to obtain the enantio-enriched target in good overall yield. The synthesis featured a key asymmetric transfer h ...

EPFL2018

Total Synthesis of Alstilobanine C, Undulifoline and Alstilobanine B

Nicolas David Gaeng

The total synthesis of pentacyclic monoterpene indole alkaloids is the focus of this thesis. Total syntheses of (±)-alstilobanine C, (±)-undulifoline and (±)-alstilobanine B, three natural products from the Ulean family of alkaloids, were accomplished. The ...

EPFL2018

Electrostatic spray ionization from 384-well microtiter plates for mass spectrometry analysis based enzyme assay and drug metabolism screening

Hubert Girault, Liang Qiao, Tzu-En Lin, Elena Tobolkina, Xiaoqin Zhong, Yan Deng, Emna Belghith

We have realized the direct ionization of samples from wells of microtiter plates under atmospheric conditions for mass spectrometry analysis without any liquid delivery system or any additional interface. The microtiter plate is a commercially available 3 ...

American Chemical Society2017

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Silver nitrate-catalyzed reaction of methyl α,α-disubstituted α-isocyanoacetates with primary amines afforded 3,5,5-trisubstituted imidazolones in good to excellent yields. A silver salt-catalyzed insertion of the isocyano group into the N−H bond of the am ...

American Chemical Society2017