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 International Edition

DOI: 10.1002/anie.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: $5,510

Funders: Deutsche Forschungsgemeinschaft, Studienstiftung des Deutschen Volkes