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

Nicolai Cramer, Matthew Wodrich

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

Nicolai Cramer, Matthew Wodrich

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

Jérôme Waser, Matthew Wodrich, 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

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

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

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

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

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

Jérôme Waser, Matthew Wodrich

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

Matthew Wodrich, Rubén Laplaza Solanas, Anne-Clémence Corminboeuf

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

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