Publications related to Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates

Related publications (20)

Development of synthetic methods starting from cyclopropenes: taming cyclopropyl radical, cyclopropyl and cyclopropenium cations

Due to the high ring strain and unique bonding, cyclopropenes represent important 3-carbon synthons in organic synthesis. Intrigued by the unique reactivity of cyclopropenes, we were interested in further exploration of their chemical properties. Trying to ...

EPFL2025

Radical-Mediated Azidation of Benzylic C-H Bonds and Azidofunctionalization of Alkenes

Pierre Gérard Joseph Palamini

Organic azides are known for their reactivity and broad applicability in organic synthesis. These compounds are pivotal in various chemical transformations, including nucleophilic substitution and cycloaddition reactions. Beyond synthetic chemistry, organi ...

EPFL2025

Silylium-Catalyzed Activation of DonorAcceptor Strained Rings and Annulation with Indoles

Jérôme Waser, Emma Gabrielle Louise Robert

: Leveraging the unique reactivity profile of donor -acceptor aminocyclopropanes and cyclobutanes allows the preparation of complex nitrogen -substituted molecules. While most reports focus on donor -acceptor strained rings with two geminal carbonyl groups ...

Swiss Chemical Soc2024

Doping In Vivo Alkylation in E. coli by Introducing the Direct Sulfurylation Pathway of S. cerevisiae

Patricia Bencic

Methylation and alkylation are important techniques used for the synthesis and derivatisation of small molecules and natural products. Application of S-adenosylmethionine (SAM)-dependent methyltransferases (MTs) in biotechnological hosts such as Escherichi ...

Wiley-VCH Verlag GmbH2024

Donor-Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium-Catalyzed (4+2) Annulation with Indoles

Jérôme Waser, Matthew Wodrich, Emma Gabrielle Louise Robert, Vincent Géry C Pirenne

A convenient one-step synthesis of beta-aminocyclobutane monoesters starting from commercially available reagents is reported. The obtained strained rings undergo (4+2) dearomative annulation with indole partners using silylium catalysis. This organocataly ...

Wiley-VCH Verlag GmbH2023

Hypervalent Iodine: New Reagents and Functionalization of Peptides

Eliott Hugo Joran Le Du

Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ide ...

EPFL2023

Photochemical [2+2] Cycloaddition of Alkynyl Boronates

Oleksandr Liashuk, Jérôme Waser

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

Isolation, Characterisation and Reactivity of N-Heterocyclic Diazoolefins

Paul Varava

Examples for applications of nitrous oxide in organic synthesis remain rare up until today. First mayor contributions of our group were published in 2012, when nitrous oxide was successfully captured by N-heterocyclic carbenes. Subsequent studies investiga ...

EPFL2022

Catalytic Enantioselective Synthesis of Morpholinones Enabled by Aza-Benzilic Ester Rearrangement

Jieping Zhu, Qian Wang, Hua Wu

Chiral morpholinone is an important building block in organic synthesis and a pharmacophore in medicinal chemistry. However, catalytic enantioselective methods for the construction of this N,O-heterocycle remain scarce. We report herein a chiral phosphoric ...

2021

Palladium-Catalyzed Multicomponent Synthesis of Fully Substituted Alkylidene Furanones

Qian Wang, Jieping Zhu, Ruben Omar Torres Ochoa

In the presence of a catalytic amount of Pd(OAc)(2) and XantPhos, the three-component reaction of ynones, imines, and aryl iodides affords fully substituted alkylidene-furan-3(2H)-ones via a sequence of the Mannich reaction followed by chemo- and regiosele ...

AMER CHEMICAL SOC2020

1,3,2‐Diazaphospholenes Catalyze the Conjugate Reduction of Substituted Acrylic Acids

Nicolai Cramer, John Henry Reed

The potent nucleophilicity and remarkably low basicity of 1,3,2- diazaphospholenes (DAPs) is exploited in a catalytic, metal-free 1,4-reduction of free ,-unsaturated carboxylic acids. Notably, the reduction occurs without a prior deprotonation of the car ...

Wiley-VCH Verlag2020

Design of Surface-Supported Bio-inspired Networks for CO2 and O2 Activation at Room Temperature

Daniel Eduardo Hurtado Salinas

The structure of a biological system defines its function. Therefore, nature has developed sophisticated systems that catalyze chemical reactions that are vital for life on earth. For instance, the photosynthesis is a biological process that is partially r ...

EPFL2018

Organocatalytic Nucleophilic Addition of Hydrazones to Imines: Synthesis of Enantioenriched Vicinal Diamines

Jieping Zhu, Qian Wang, Yang Wang

In the presence of a catalytic amount of chiral phosphoric acid, nucleophilic addition of N-monosubstituted hydrazones to N-Boc imines affords differentially protected vicinal diamines in the form of b-amino N,N’-dialkyldiazenes in excellent yields with hi ...

Wiley-Blackwell2017

Switchable [3+2] and [4+2] Heteroannulation of Primary Propargylamines with Isonitriles to Imidazoles and 1,6-Dihydropyrimidines: Catalyst Loading Enabled Reaction Divergence

Jieping Zhu, Qian Wang, Shuo Tong

Isonitrile 1 due to its carbene-like reactivity serves generally as a one-carbon synthon in a diverse set of organic transformations. We report in this article that the isocyano group can also act as a polarized triple bond to undergo, as a two-atom syntho ...

Wiley-Blackwell2016

Organocatalytic Enantioselective Vinylogous Pinacol Rearrangement Enabled by Chiral Ion Pairing

Jieping Zhu, Qian Wang, Hua Wu

An enantioselective pinacol rearrangement of functionalized (E)-2-butene-1,4-diols was developed. In the presence of a catalytic amount of a chiral BINOL-derived N-triflyl phosphoramide, these 1,4-diols rearranged to b,g-unsaturated ketones in excellent yi ...

Wiley-Blackwell2016

On the Formation and Transformation of alpha-Iminonitriles, the Desymmetrization of Bicyclic Bislactones and Total Synthesis of (-)-Leucomidine B and (-)-Rhazinilam

Jean-Baptiste Gualtierotti

Two principle topics are covered in this thesis. The first section deals with the development of novel synthetically useful multicomponent reactions. The development of three multicomponent reactions, based on α-iminonitriles, is presented. The first descr ...

EPFL2014

Synthesis of Multifunctionalized 1,2,3,4-Tetrahydropyridines, 2,3-Dihydropyridin-4(1H)-ones, and Pyridines from Tandem Reactions Initiated by [5+1] Cycloaddition of N-Formylmethyl-Substituted Enamides to Isocyanides: Mechanistic Insight and Synthetic Application

Jieping Zhu

Tandem reactions for the efficient synthesis of multifunctionalized 1,2,3,4-tetrahydropyridines, 2,3-dihydropyridin-4(1H)-ones, and pyridine derivatives have been developed and reaction mechanisms have been investigated. Synthetic cascades are initiated by ...

Wiley-Blackwell2013

Pyridine-Based Lanthanide Complexes Combining MRI and NIR Luminescence Activities

Lothar Helm, Jian Zhang

A series of novel triazole derivative pyridine-based polyaminopolycarboxylate ligands has been synthesized for lanthanide complexation. This versatile platform of chelating agents combines advantageous properties for both magnetic resonance (MR) and optica ...

2012

Reactivity Of Arylnitrile Oxides And C-Aroyl-N-Phenylnitrones With 3-Methylenedihydro-(3H)-Furan-2-One And Itaconic Anhydride

Christophe Roussel

1,3-dipolar cycloaddition is a powerful route for the synthesis of five-membered heterocycles. The [3+2] cycloadditions of some alpha-methylene-gamma-buryrolactones, namely 3-methylenedihydro-(3H)-furan-2-one (1) and itaconic anhydride (2) were Studied. Th ...

2009

Aza-Annulation Strategies in Alkaloid Total Synthesis

Karl Gademann

This review highlights the synthesis of nitrogen-containing natural products via aza-annulation. Strategic, tactical, and methodological perspectives are discussed, including recent developments such as metal- or organocatalyzed reactions, oxidative or red ...

Georg Thieme Verlag2008