Dienamine-Catalyzed Nitrone Formation via Redox Reaction

Americo J. Fraboni, Stacey E. Brenner-Moyer

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The first catalytic method to directly introduce nitrone functionality onto aldehyde substrates is described. This reaction proceeds by an unprecedented organocatalytic redox mechanism in which an enal is oxidized to the -nitrone via dienamine catalysis, thereby reducing an equivalent of nitrosobenzene. This reaction is a unique example of divergent reactivity of an enal, which represents a novel strategy for rapidly accessing small libraries of N,O-heterocycles. Alternatively, divergent reactivity can be suppressed simply by changing solvents.

Original languageEnglish (US)
Pages (from-to)2146-2149
Number of pages4
JournalOrganic letters
Volume18
Issue number9
DOIs
StatePublished - May 6 2016

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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