Publications related to Laboratory of Synthesis and Natural Products

Development of methods for the synthesis of large combinatorial libraries of macrocyclic compounds

Macrocycles have raised much interest in the pharmaceutical industry due to their ability to bind challenging targets while often still being able to cross membranes to reach intracellular proteins. However, the development of macrocyclic ligands to new di ...

EPFL2023

New Cu (I) complexes as catalyst for "click" reaction: An experimental and computational study

Farzaneh Fadaei Tirani

In this work, two novel well-defined Cu (I) complexes of a Schiff base ligand are described. For this purpose, N, N '-bis (trans-cinnamaldehyde) ethylenediimine [C20H20N2] (L) and Cu (I) complex of the type [CuC20H20N2)PPh3Cl] (C1) and [Cu(C20H20N2)PPh3Br] ...

WILEY2023

Asymmetric Construction of α,α‐Disubstituted Piperazinones Enabled by Benzilic Amide Rearrangement

Jieping Zhu, Hua Wu, Yuping He

An unprecedent asymmetric catalytic benzilic amide rearrangement for the synthesis of α,α-disubstituted piperazinones is reported. The reaction proceeds via a domino [4+1] imidazolidination/formal 1,2-nitro- gen shift/1,2-aryl or alkyl migration sequence, ...

2023

Cycloalkane Oxidation Catalyzed by Copper-based Catalysts with H2O2 under Mild Conditions

Nukorn Plainpan, Jantira Chimlert

Copper-catalyzed cycloalkane oxidation using H2O2 as an oxidant was investigated under mild conditions. The copper catalysts studied in this work ranged from commercially-available copper(II) salts to copper(II) complexes containing polypyridyl ligands. Va ...

WILEY-V C H VERLAG GMBH2023

Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling

Paul Joseph Dyson, Mingyang Liu

Efficient valorization of lignin, a sustainable source of functionalized aromatic products, would reduce dependence on fossil-derived feedstocks. Oxidative depolymerization is frequently applied to lignin to generate phenolic mono- mers. However, due to th ...

2023

Organocatalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoesters: Development and Application to the Total Synthesis of (+)‐Alstratine A

Qian Wang, Jieping Zhu, Rémi Julien Sylvain Andres, Fenggang Sun

We report herein an asymmetric Pictet– Spengler reaction of α-ketoesters. In the presence of a catalytic amount of simple alanine-derived squaramide and p-nitrobenzoic acid, reaction of tryptamines with methyl 2-oxoalkanoates afforded the corresponding 1- ...

2023

Bounds on scattering of neutral Goldstones

Andrea Guerrieri, Denis Karateev, Kelian Philippe Häring

We study the space of

2\to 2

scattering amplitudes of neutral Goldstone bosons in four space-time dimensions. We establish universal bounds on the first two non-universal Wilson coefficients of the low energy Effective Field Theory (EFT) for such particl ...

2023

Copper (I)‐BOX Catalyzed Asymmetric 3‐Component Reaction for the Synthesis of Trifluoromethylated Propargylic Ethers and Anilines**

Jérôme Waser, Nieves Pilar Ramirez Hernandez

An asymmetric 3-component reaction between EthynylBenziodoXoles (EBXs), 2,2,2-trifluorodiazoethane and nucleophiles catalyzed by a CuI-BOX (Bisoxazoline) catalyst is described. This protocol gives access to chiral trifluoromethylated propargyl ethers and a ...

2023

Terminal 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 GMBH2023

A Simple, Transition Metal Catalyst-Free Method for the Design of Complex Organic Building Blocks Used to Construct Porous Metal-Organic Frameworks

Wendy Lee Queen, Jordi Espin Marti, Jocelyn Richard Roth, Till Marian Schertenleib, Nazanin Taheri, Ilia Kochetygov, Anita Justin, Sophia Alessandra Pache

The design of metal-organic frameworks (MOFs) having large pore sizes and volumes often requires the use of complex organic ligands, currently synthesized using costly and time-consuming palladium-catalyzed coupling chemistry. Thus, in the present work, a ...

WILEY-V C H VERLAG GMBH2023

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Development of methods for the synthesis of large combinatorial libraries of macrocyclic compounds

New Cu (I) complexes as catalyst for "click" reaction: An experimental and computational study

Asymmetric Construction of α,α‐Disubstituted Piperazinones Enabled by Benzilic Amide Rearrangement

Cycloalkane Oxidation Catalyzed by Copper-based Catalysts with H2O2 under Mild Conditions

Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling

Organocatalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoesters: Development and Application to the Total Synthesis of (+)‐Alstratine A

Bounds on scattering of neutral Goldstones

Copper (I)‐BOX Catalyzed Asymmetric 3‐Component Reaction for the Synthesis of Trifluoromethylated Propargylic Ethers and Anilines**

Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B

A Simple, Transition Metal Catalyst-Free Method for the Design of Complex Organic Building Blocks Used to Construct Porous Metal-Organic Frameworks

Development of methods for the synthesis of large combinatorial libraries of macrocyclic compounds

New Cu (I) complexes as catalyst for "click" reaction: An experimental and computational study

Cycloalkane Oxidation Catalyzed by Copper-based Catalysts with H2O2 under Mild Conditions

Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling

Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B

Asymmetric Construction of α,α‐Disubstituted Piperazinones Enabled by Benzilic Amide Rearrangement

Organocatalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoesters: Development and Application to the Total Synthesis of (+)‐Alstratine A

Bounds on scattering of neutral Goldstones

A Simple, Transition Metal Catalyst-Free Method for the Design of Complex Organic Building Blocks Used to Construct Porous Metal-Organic Frameworks

Copper (I)‐BOX Catalyzed Asymmetric 3‐Component Reaction for the Synthesis of Trifluoromethylated Propargylic Ethers and Anilines**