Catalytic Deracemization of 1,2-Aminoalcohols through Enantioselective Hydrogen Atom Abstraction.

ABSTRACT: Catalytic deracemization appears a superficially simple way to obtain enantioenriched chiral compounds but is deceptively challenging. The popularization of photochemical methods which utilize excited state pathways have permitted breakthroughs, but application to simple functional motifs that constitute common chiral building blocks is still rare. We report the catalytic deracemization of N-acyl-1,2-aminoalcohols using a cinchona alkaloid-derived catalyst that operates through enantioselective hydrogen atom abstraction, once oxidized by an excited photocatalyst. In combination with an achiral thiol to return the hydrogen atom, accumulation of the unreactive enantiomer occurs. Our catalyst exhibits extremely high chemoselectivity for abstraction adjacent to alcohols and permits a ra

SUBMITTER: Davies DJ 

PROVIDER: S-EPMC12814349 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature