Enantioselective anti-Carboboration of Alkenyl Amides – Now In Press

Over the past two years our lab and other labs around the world have been working hard to develop strategies for controlling enantioselectivity in palladium-catalyzed directed hydrofunctionalization and 1,2-difunctionalization reactions. Last month, we described a Pd(II)/chiral phosphoric acid system for enantioselective hydrofunctionalization with prochiral nucleophiles (click here). In a manuscript appearing online today in ACS Catalysis, we describe a new method for enantioselective anti-carboboration, representing the first time that a 1,2-difunctionalization within this family of reactions has been rendered enantioselectivity (click here). We also propose a new mechanistic model based on stoichiometric experiments to account for the stereoconvergent nature of the transformation. Congrats to all of the authors, Zhen, Xiaohan, and Tian (May). Special props to our two undergrad co-authors, Xiaohan and May! In case anyone missed it, a pre-print of this work was published on ChemRxiv back in early January (click here).

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Josh completes his undergrad internship

After a fun and productive six months in San Diego, Tianhua (Josh) Tang, finished his internship and now returns to Nankai University in Tianjin, China, to write his undergraduate thesis before graduating this spring. After earning his Bachelor’s degree, Josh will return to the US pursue his Ph.D. in organic chemistry (location TBD). During his time in the Engle lab, Josh worked under the mentorship of Mingyu and made significant contributions to the development of new catalytic alkyne functionalization methods. Outside of the lab, he enjoyed learning about American culture from his many friends in the lab and sampling the myriad restaurants in San Diego, including the various Chinese restaurants in Kearny Mesa.