UW-Madison Department of Chemistry
Cade and Omar report the results of a collaboration with GSK showing that adamantane dicarboxylates are accessible feedstock building blocks for the rapid assembly of novel bioisosteres for meta-disubstituted arenes. The report is now live on Chem Sci.
Proud to present Riley’s design for a modular, synthetically flexible, and intuitively tunable chiral photocatalyst based on the canonical PyBox family of chiral Lewis acid catalysts. Thanks to Lea Hämmerling and Eli Zysman-Coleman for a terrific collaboration. See our full report on the use of RyBox in Science.
Tahoe, Omar, and Jesse report a new approach to oxetane synthesis that turns the classical mechanism of the Paternò–Büchi reaction on its head. Proud of our contribution to the 15th anniversary Chem Sci collection.
How do you functionalize a C–C bond? Cade, Caitlin, Matthieu, and Felix have a compelling method for migrating an oxygen atom into an unstrained C(sp3)–C(sp3) bond. In cyclic contexts, this enables the editing of a saturated carbocycle into a ring-expanded heterocycle. In acyclic contexts, it enables the permutation of the heavy atoms in a hydroxymethyl …
In our second collaborative publication with the Paton group as part of SuPRCat, Katie led a terrific team (Rodrigo, Mihai, Grace, and Sam) to show that base-metal complexes of carboxylic acids can engage in direct C–H lactonizations reactions upon LMCT photoactivation. The surprising mechanistic insight from these experiments is that the reaction does not involve …
In a terrific collaborative project with Eli Lilly and the Stahl lab, Caitlin, Max, and Dylan report a method for the synthesis of modified carbohydrates through metallaphotoredox cross-ketonization. Interestingly, this study revealed a profound dependence on precise temperature control, which we posit may be of similar importance in any dual-catalyst metallaphotoredox reaction. Now in Chem …
Ellie, Zoe, and Rodrigo report a Brønsted acid catalyzed asymmetric [2π + 2σ] cycloaddition in JACS, providing a straightforward route to rigid chiral bicycles in highly enantioenriched form. A terrific collaboration with GSK and Corteva through the SynCat consortium.
Our star undergraduate Rodrigo wondered if a commercial chiral Brønsted acid could be used in our asymmetric photochemistry instead of the optimal BINOL-derived triflimide we originally used. The answer is yes! Rodrigo reports the enantioselective synthesis of δ-truxinates on 2 gram scale in Org Syn. Special thanks to Yu-Che Chang in the Brown group for …
Alana, Mihai, and Arindam formed an unstoppable collaboration team through the SuPRCat CCI with the Paton and Damrauer groups to understand a new, remarkably general method for photocatalytic alkene aziridination. A combination of preparative, computational, and spectroscopic studies paint a very clear picture of this reaction mechanism. Now live on ACS Catalysis.
We had a great collaboration with the Schmidt group on an AI model for predicting the emission spectra of Ir complexes. Based on a big data set collected and published by the Bernhard group. Now on ChemPhysChem!