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

## TL;DR

A new light-driven method creates chiral aminoalcohols with high precision, useful for making bioactive molecules.

## Contribution

A metal-free photoredox Minisci strategy for enantiopure 2-hetaryl-1,2-aminoalcohols with stereoretention.

## Key findings

- The method achieves complete stereoretention in radical α-hetarylation under visible light.
- Facial selectivity is governed by CH/π interactions between heteroarene and bridgehead methyl group.
- The process is scalable and generates medicinally relevant scaffolds.

## 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 versatile
precursors to medicinally relevant scaffolds, and the scalability
of the process highlights its synthetic utility. This work establishes
a broadly applicable platform for the stereocontrolled radical functionalization
of amino acid derivatives.