Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible-Light Photocatalysis

Phillip Trieu, William H. Filkin, Ali Pinarci, Elisa M. Tobias, Rufai Madiu, Brandon Dellosso, Justin Roldan, Pulakesh Das, Brooke E. Austin, Gustavo Moura-Letts

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Herein we report the first redox-neutral visible-light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible-light-promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)3Cl2, with the reaction proceeding with high yields and good selectivities. A redox-neutral pathway is proposed as the primary photoredox mechanism for this transformation.

Original languageEnglish (US)
Article numbere202200277
JournalChemPhotoChem
Volume7
Issue number3
DOIs
StatePublished - Mar 2023

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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