Work

Photochemical Deracemization of N ‐Carboxyanhydrides En Route to Chiral α‐Amino Acid Derivatives

Year: 2024

Type: article

Abstract: Readily accessible, racemic N ‐carboxyanhydrides (NCAs) of α‐amino acids underwent a deracemization reaction upon irradiation at λ=366 nm in the presence of a chiral benzophenone catalyst. The enantioenriched NCAs (up to 98 % ee ) serve as activated α‐amino acid surrogates and, due to their instability, they were directly converted into consecutive products. N ‐Protected α‐amino acid esters were obtained after reaction with MeOH and N ‐benzoylation (14 examples, 70 %‐ quant ., 82–96 % ee ). Other consecutive reactions included amide (ten examples, 65 %‐ quant ., 90–98 % ee ) and peptide (three examples, 75–89 %, d. r.=97/3 to 94/6) bond formation. Limitations of the method relate for some NCAs to issues with solubility, photooxidation, and high configurational lability.

Source: Angewandte Chemie

DOI: 10.1002/ange.202418873

Authors: Maximilian Iglhaut, Philip Freund, Thorsten Bach

Institution: Technical University of Munich

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,250

Funders: Deutsche Forschungsgemeinschaft, Studienstiftung des Deutschen Volkes