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

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Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C-H Bond Formation

Jérôme Waser, Mikus Purins, Ashis Kumar Das, Luca Buzzetti

We report an enantioselective palladium-catalyzed trans-hydroalkoxylation of propargylic amines with a trifluoroacetaldehydederived tether to build chiral oxazolidines. Diastereoselective hydrogenation using a heterogeneous palladium catalyst then gave acc ...

2022

Rh-catalyzed C-H Bond Heteroarylation with Hypervalent Iodine Reagents and Pd-Catalyzed Tethered Functionalizations of Carbon-Carbon Multiple Bonds

Ashis Kumar Das

Transition metal-catalyzed C-H activation is a powerful tool for the synthesis of organic building blocks, materials, and natural products. Over the last decade, directing-group-assisted metal-catalyzed C-H functionalization has attracted increasing intere ...

EPFL2022

Enantio- and diastereoselective construction of vicinal C(sp(3)) centres via nickel-catalysed hydroalkylation of alkenes

Xile Hu, Chao Fan, Srikrishna Bera

In drug discovery, the proportion of aliphatic carbons (C(sp(3))) and the presence of chiral carbons in organic molecules are positively correlated to their chance of clinical success. Although methods exist for the synthesis of chiral C(sp(3))-rich molecu ...

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

Chiral Cyclic Alkyl Amino Carbene (CAAC) Transition-Metal Complexes: Synthesis, Structural Analysis, and Evaluation in Asymmetric Catalysis

Adrien Jules Louis Madron Du Vigné

Despite recent advances in the field of cyclic alkyl amino carbenes (CAACs) including a few complementary synthetic strategies affording CAACs with various substitution patterns, the application potential of chiral CAACs to efficiently catalyze asymmetric ...

2022

Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols

Xile Hu, Zhikun Zhang

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols whic ...

Wiley-VCH Verlag GmbH2021

Asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces

Harald Brune, Roland Hany, Roland Widmer, Michael Bauer, Samuel Thomas Stolz

Achieving fundamental understanding of enantioselective heterogeneous synthesis is marred by the permanent presence of multitudinous arrangements of catalytically active sites in real catalysts. In this study, we address this issue by using structurally co ...

NATURE RESEARCH2021

Asymmetric Elimination Reaction on Chiral Metal Surfaces

Harald Brune, Roland Widmer, Martina Danese, Daniele Passerone, Samuel Thomas Stolz

The production of enantiopure materials and molecules is of uttermost relevance in research and industry in numerous contexts, ranging from nonlinear optics to asymmetric synthesis. In the context of the latter, dehalogenation, which is an essential reacti ...

Wiley-V C H Verlag Gmbh2021

Developing the Catalytic Applications of 1,3,2-Diazaphospholenes

John Henry Reed

The development of new catalytic methods for organic synthesis is a critical endeavour in order to obviate the economic and ecological drawbacks of stoichiometric organic synthesis. While catalysis can offer significant advantages in terms of atom-economy, ...

EPFL2021

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Xile Hu, Srikrishna Bera, Deyun Qian

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation metho ...

AMER CHEMICAL SOC2021

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Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C-H Bond Formation

Jérôme Waser, Mikus Purins, Ashis Kumar Das, Luca Buzzetti

2022

Rh-catalyzed C-H Bond Heteroarylation with Hypervalent Iodine Reagents and Pd-Catalyzed Tethered Functionalizations of Carbon-Carbon Multiple Bonds

Ashis Kumar Das

EPFL2022

Chiral Cyclic Alkyl Amino Carbene (CAAC) Transition-Metal Complexes: Synthesis, Structural Analysis, and Evaluation in Asymmetric Catalysis

Adrien Jules Louis Madron Du Vigné

2022