Virtual Lecture: Synthesis Through C-C Scission

Lecture held on: June 6, 2024

Presenter

Prof. Ohyun Kwon – University of California

In this lecture, Prof. Ohyun Kwon discussed radical chemistry based on C-C bond scission. The lecture began with another area of research endeavors in Prof. Ohyun Kwon’s group-phosphorus organocatalysis. It then presented how their need to create chiral phosphines, CarvoPhos, of particular configuration inspired their invention of a series of new reactions based on C-C bond cleavage. To be specific, they have implemented one-pot processes to oxidize alkenes into a-methoxyhydroperoxides, for subsequent Fe(II) mediated reductive fragmentations that yield alkyl radical intermediates. Most recently, they have implemented a pathway for the Cu(I)-catalyzed dealkenylative amination for the late-stage modification of hormones, pharmaceutical reagents, peptides, and nucleosides. A commodity chemical, a-methylstyrene ($3.90/mol)- a by-product in the cumene process-served as the methylation reagent to prepare methylated nucleosides directly from canonical nucleosides in a single-step synthesis. In turn, Prof. Ohyun Kwon’s team synthesized several non-trivial primary amines from readily-accessible terpenoids.