Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis

Graham Haun, Alyson N. Paneque, David W. Almond, Brooke E. Austin, Gustavo Moura-Letts

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

This effort reports the first redox-neutral visible-light photocatalytic intramolecular dipolar cycloaddition for the diastereoselective synthesis of chromenoisoxazolidines. The authors have found that alkenylphenyl nitrones with a diverse substitution pattern on the aromatic ring and the alkenyl substituent undergo visible-light-promoted cycloadditions in the presence of catalytic amounts of Ru(bpy) 3 Cl 2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.

Original languageEnglish (US)
Pages (from-to)1388-1392
Number of pages5
JournalOrganic Letters
Volume21
Issue number5
DOIs
StatePublished - Mar 1 2019

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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