Single-Step Synthesis of γ-Ketoacids through a Photoredox-Catalyzed Dual Decarboxylative Coupling of α-Oxo Acids and Maleic Anhydrides.

Autor: Davies AM; Department of Chemistry, The University of Kansas, 1567 Irving Hill Rd., Lawrence, Kansas 66045, United States., Londhe SS; Department of Chemistry, The University of Kansas, 1567 Irving Hill Rd., Lawrence, Kansas 66045, United States., Smith ER; Department of Chemistry, The University of Kansas, 1567 Irving Hill Rd., Lawrence, Kansas 66045, United States., Tunge JA; Department of Chemistry, The University of Kansas, 1567 Irving Hill Rd., Lawrence, Kansas 66045, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Dec 08; Vol. 25 (48), pp. 8634-8639. Date of Electronic Publication: 2023 Nov 22.
DOI: 10.1021/acs.orglett.3c03258
Abstrakt: A photocatalytic methodology for the single step synthesis of γ-ketoacids from α-ketoacids has been developed. This method employs maleic anhydrides as traceless synthetic equivalents of acrylic acids, achieving a selective cross-coupling via a dual decarboxylative strategy, where molecular CO 2 is released as the only waste byproduct. The method has also been expanded to incorporate a highly regioselective, 3-component coupling with various alcohols to access functionalized γ-ketoesters.
Databáze: MEDLINE