Accessing α-Amino Ketyl Radicals from β-Amino Alcohols via Chemoselective Hydrogen Atom Transfer Catalysis

Abstract

The selective activation of a given C–H bond in complex molecules possessing bonds of similar polarity and strength remains one of the foremost challenges in hydrogen atom transfer (HAT) catalysis. Herein, we present the combination of photoredox and HAT catalysis with an oxophilic boron-based catalyst to achieve the chemoselective abstraction of α-hydroxy C–H bonds in β-amino alcohols. This enables us to access α-amino ketyl radicals, which are exploited for the direct synthesis of γ-oxo-δ-amino esters─a prominent scaffold in biologically active molecules.