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Related Experiment Video

Updated: Jul 15, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Thermal and catalyzed [3,3]-phosphorimidate rearrangements.

Bin Chen1, Anna K Mapp

  • 1Departments of Chemistry and Medicinal Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.

Journal of the American Chemical Society
|May 5, 2005
PubMed
Summary

This study introduces a novel [3,3]-rearrangement of allylic phosphorimidates for synthesizing stereodefined allylic amines. This efficient three-component reaction offers a new pathway for creating complex nitrogen-containing molecules.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Asymmetric Synthesis

Background:

  • [3,3]-Sigmatropic rearrangements are powerful tools for C-C bond formation.
  • Selective C-N bond formation via [3,3]-rearrangements remains underdeveloped.
  • Stereodefined allylic amines are valuable synthetic targets.

Purpose of the Study:

  • To develop a novel [3,3]-rearrangement for selective C-N bond formation.
  • To access stereodefined allylic amines efficiently.
  • To explore the scope and mechanism of this new reaction.

Main Methods:

  • In situ generation of allylic phosphorimidates from allylic alcohols, chlorophosphites, and organic azides.
  • Three-component reaction strategy.
  • Stereochemical analysis to confirm fidelity of stereochemical transfer.

Main Results:

  • A new [3,3]-rearrangement of allylic phosphorimidates was established.
  • Stereodefined allylic amines were synthesized with high fidelity.
  • The reaction proceeds via an intramolecular mechanism.
  • Electron-deficient groups or transition-metal catalysis enhance reaction efficiency.

Conclusions:

  • This work provides an efficient three-component method for synthesizing stereodefined allylic amines.
  • The reaction offers a versatile platform for accessing diverse allylic amine structures.
  • The methodology expands the utility of [3,3]-rearrangements for C-N bond formation.