Author: tyoon

Truxinate Org Syn Prep

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 …

Understanding photocatalytic aziridination

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.  

Predicting Ir emissions using AI

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!

Asymmetric Paternò–Büchi Reaction

Jesse, Tahoe, Wes, and Yerin have a terrific new paper in JACS today about the long road to an asymmetric catalytic Paternò–Büchi reaction. A great collaboration with Kent and the Wright lab at UW.

Solid-state synthesis of the truxillates

In JACS today, Ellie, Hyung Joo, and Matt report a general approach to the truillate family of natural products enabled by solid state photochemistry. Synthetically, this paper complements the route to the truxinates we published last year and provides comprehensive control over the construction of the large class of dimeric cyclobutane natural products. Special thanks …

Enantioselective 6π Photoelectrocyclizations

The latest chapter in our ongoing collaboration with the Baik group is now published in JACS. Wes and Hanna lead a comprehensive synthetic, spectroscopic, and computational study of highly enantioselective 6π photoelectrocyclizations. Previously on the Rxiv.

Cu oxidant review

A coda to Grace’s successful PhD career: her review describing the use of Cu(II) salts as terminal oxidants in photochemical reactions is online at OBMC.

General synthesis of the truxinates

Part of the motivation for continued development of enantioselective photocatalysis has been the possibility of streamlining the synthesis of densely substituted small-ring compounds. Matt, Matthew, and Herman have devised a demonstration of this principle by completing the convergent enantio-, diastereo-, chemo-, and regioselective synthesis of five natural products. See the report online now at JACS.

Allylic amination

Grace, Ellie, and Nic have leveraged an unexpected observation into an unusual method for allylic amination using Cu(II)-mediated radical–polar crossover.  Online now at OL!

Photosensitized De Mayo reactions

Riley, Andrew, and Eunji’s study showing how Lewis acids can improve the scope of sensitized De Mayo reactions is online at Org Lett!