Photocatalytic Minisci Approach to Chiral 2-Hetaryl-1,2-aminoalcohols from β-Hydroxy-α-amino Acid-Derived Redox Active Esters.

ABSTRACT: Chiral 1,2-aminoalcohols are privileged motifs in bioactive molecules, yet their stereocontrolled synthesis remains a challenge. Here, we report a general, metal-free photoredox Minisci strategy that converts bicyclic N,O-acetals derived from β-hydroxy-α-amino acids into enantiopure 2-hetaryl-1,2-aminoalcohols with complete stereoretention. This diastereoselective radical α-hetarylation proceeds under visible light and mild conditions, tolerating diverse substitution patterns on both the heteroarene and the bicyclic scaffold. Combined experimental and quantum mechanical studies reveal that dispersion (CH/π) interactions between the incoming heteroarene and the bridgehead methyl group govern the unexpected facial selectivity in the C-C bond-forming step. The products serve as

SUBMITTER: Oroz P 

PROVIDER: S-EPMC12624844 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature