Publications de Matthew Wodrich

Chiral Phosphoric Acid-catalyzed Enantioselective Higher-order Cycloadditions: Temperature-dependent Periselectivity

Higher-order cycloadditions (HOCs) are powerful tools for constructing complex cyclic structures, but their synthetic utility is often limited by poor periselectivity and challenges in achieving high diastereo- and enantioselectivity. Herein, we report a c ...

AMER CHEMICAL SOC2025

Enantioselective acyl-trifluoromethylation of olefins by bulky thiazolium carbene catalysis

Matthew Wodrich, Nicolai Cramer

Enantioenriched α-chiral β-fluorinated ketones are valuable structural motifs with application in several fields. The recently emerged concept of NHC-catalyzed radical acyl-trifluoromethylation of olefins offers a rapid route to construct racemic β-fluorin ...

2025

Enantioselective Cobalt(III)-Catalyzed [4 + 1] Annulation of Benzamides: Cyclopropenes as One-Carbon Synthons

Matthew Wodrich, Nicolai Cramer

A chiral cyclopentadienyl cobalt(III)-catalyzed enantioselective [4 + 1] annulation of N-chlorobenzamides with cyclopropenes is reported. The cobalt catalyst engages in the C−H activation as well as promotes the C−C bond cleavage of the cyclopropene, rende ...

American Chemical Society (ACS)2025

Accessing elusive σ-type cyclopropenium cation equivalents through redox gold catalysis

Matthew Wodrich, Jérôme Waser, Xiangdong Li

Cyclopropenes are the smallest unsaturated carbocycles. Removing one substituent from cyclopropenes leads to cyclopropenium cations (C3 + systems, CPCs). Stable aromatic pi-type CPCs were discovered by Breslow in 1957 by removing a substituent on the aliph ...

2024

From Organic Fragments to Photoswitchable Catalysts: The OFF-ON Structural Repository for Transferable Kernel-Based Potentials

Anne-Clémence Corminboeuf, Matthew Wodrich, Raimon Fabregat I De Aguilar-Amat, Veronika Juraskova, Simone Gallarati, Frédéric Célerse

Structurally and conformationally diverse databases are needed to train accurate neural networks or kernel-based potentials capable of exploring the complex free energy landscape of flexible functional organic molecules. Curating such databases for species ...

Amer Chemical Soc2024

Enantiospecific Synthesis of Planar Chiral Rhodium and Iridium Cyclopentadienyl Complexes: Enabling Streamlined and Computer-Guided Access to Highly Selective Catalysts for Asymmetric C-H Functionalizations

Rosario Scopelliti, Anne-Clémence Corminboeuf, Matthew Wodrich, Nicolai Cramer, Farzaneh Fadaei Tirani, Aragorn Nathan Laverny, Rubén Laplaza Solanas

Chiral cyclopentadienyl (CpX) metal complexes are frequently used in asymmetric catalysis by virtue of their high reactivity and selectivity. Planar-chiral-only rhodium and iridium cyclopentadienyl complexes are particularly promising due to unrestricted c ...

2024

Microkinetic Molecular Volcano Plots for Enhanced Catalyst Selectivity and Activity Predictions

Anne-Clémence Corminboeuf, Matthew Wodrich, Shubhajit Das, Rubén Laplaza Solanas

Molecular volcano plots, which facilitate the rapid prediction of the activity and selectivity of prospective catalysts, have emerged as powerful tools for computational catalysis. Here, we integrate microkinetic modeling into the volcano plot framework to ...

Amer Chemical Soc2024

Homologation of Alkenyl Carbonyls via a Cyclopropanation/Light-Mediated Selective CÀ C Cleavage Strategy

Matthew Wodrich, Jérôme Waser

We report herein our studies on the direct photoactivation of carbonyl cyclopropanes to give biradical intermediates, leading to selective cleavage of the more substituted carbon-carbon bond. Depending on the substrate structure, extended alkenes were isol ...

Wiley2024

Overcoming the Pitfalls of Computing Reaction Selectivity from Ensembles of Transition States

Anne-Clémence Corminboeuf, Matthew Wodrich, Rubén Laplaza Solanas

The prediction of reaction selectivity is a challenging task for computational chemistry, not only because many molecules adopt multiple conformations but also due to the exponential relationship between effective activation energies and rate constants. To ...

2024

Reaction-Agnostic Featurization of Bidentate Ligands for Bayesian Ridge Regression of Enantioselectivity

Anne-Clémence Corminboeuf, Matthew Wodrich, Jérôme Waser, Rubén Laplaza Solanas, Alexandre Alain Schöpfer

Chiral ligands are important components in asymmetric homogeneous catalysis, but their synthesis and screening can be both time-consuming and resource-intensive. Data-driven approaches, in contrast to screening procedures based on intuition, have the poten ...

Amer Chemical Soc2024

Catalytic enantioselective reductive Eschenmoser-Claisen rearrangements

Matthew Wodrich, Nicolai Cramer

An important challenge in enantioselective catalysis is developing strategies for the precise synthesis of neighboring congested all-carbon quaternary stereocenters. The well-defined transition states of [3,3]-sigmatropic rearrangements and their underlyin ...

American Association for the Advancement of Science2024

Capturing Dichotomic Solvent Behavior in Solute−Solvent Reactions with Neural Network Potentials

Anne-Clémence Corminboeuf, Matthew Wodrich, Veronika Juraskova, Shubhajit Das, Frédéric Célerse

Simulations of chemical reactivity in condensed phase systems represent an ongoing challenge in computational chemistry, where traditional quantum chemical approaches typically struggle with both the size of the system and the potential complexity of the r ...

American Chemical Society (ACS)2024

Nickel-catalyzed direct stereoselective α-allylation of ketones with non-conjugated dienes

Matthew Wodrich, Nicolai Cramer

The development of efficient and sustainable methods for the construction of carbon-carbon bonds with the simultaneous stereoselective generation of vicinal stereogenic centers is a longstanding goal in organic chemistry. Low-valent nickel(0) complexes whi ...

Nature Research2023

Theory-guided development of homogeneous catalysts for the reduction of CO2 to formate, formaldehyde, and methanol derivatives

Anne-Clémence Corminboeuf, Matthew Wodrich, Shubhajit Das, Hanna Hinrika Cramer

The stepwise catalytic reduction of carbon dioxide (CO2) to formic acid, formaldehyde, and methanol opens non-fossil pathways to important platform chemicals. The present article aims at identifying molecular control parameters to steer the selectivity to ...

2023

Reply to Comment on 'Physics-based representations for machine learning properties of chemical reactions'

Anne-Clémence Corminboeuf, Matthew Wodrich, Puck Elisabeth van Gerwen, Rubén Laplaza Solanas

Recently, we published an article in this journal that explored physics-based representations in combination with kernel models for predicting reaction properties (i.e. TS barrier heights). In an anonymous comment on our contribution, the authors argue, am ...

2023

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

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

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

X-Ray and NMR Structural Data of Ethynylbenziodoxolones (EBXs) Reagents and Their Analogues

Rosario Scopelliti, Matthew Wodrich, Jérôme Waser, Stefano Nicolai, Farzaneh Fadaei Tirani, Durga Prasada Rao Hari, Eliott Hugo Joran Le Du, Nieves Pilar Ramirez Hernandez

First synthesized in 1991, EthynylBenziodoXolones (EBXs) - cyclic hypervalent iodine reagents derived from 2-iodobenzoic acid - are now among the most versatile electrophilic alkynylation reagents. Due to their cyclic structure, these reagents exhibit enha ...

WILEY-V C H VERLAG GMBH2023

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

Matthew Wodrich, Jérôme Waser, André Bossonnet

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

Toward in silico Catalyst Optimization

Anne-Clémence Corminboeuf, Matthew Wodrich, Nicolai Cramer, Rubén Laplaza Solanas

In this minireview, we overview a computational pipeline developed within the framework of NCCR Catalysis that can be used to successfully reproduce the enantiomeric ratios of homogeneous catalytic reactions. At the core of this pipeline is the SCINE Molas ...

SWISS CHEMICAL SOC2023

The (not so) simple prediction of enantioselectivity - a pipeline for high-fidelity computations

Anne-Clémence Corminboeuf, Matthew Wodrich, Rubén Laplaza Solanas

The computation of reaction selectivity represents an appealing complementary route to experimental studies and a powerful means to refine catalyst design strategies. Accurately establishing the selectivity of reactions facilitated by molecular catalysts, ...

ROYAL SOC CHEMISTRY2022