Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

O-alkenyl hydroxylamines: a new concept for cyclofunctionalization.

Roderick W Bates1, Kanicha Sa-Ei

  • 1Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Vibahavadi-Rangsit Highway, Laksi, Bangkok 10210, Thailand. roderick@tubtim.cri.or.th

Organic Letters
|November 22, 2002
PubMed
Summary

This study details the synthesis of isooxazolidines from O-homoallylhydroxylamines using palladium and copper catalysts. Electron-withdrawing groups on the nitrogen are crucial for this transformation, yielding cis isomers with carbamate protection.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Oleraciamides A and B: Confirmation and Revision of Structures.

Journal of natural products·2026
Same author

Myrrhain A: Structural Reassignment Highlights the Relevance of Plasticizer Contamination in Chemical and Bioactivity Studies.

Organic letters·2025
Same author

Donor acceptor phenanthrenes and benzoquinolines: synthesis by C-H activation and their photophysical properties.

Organic & biomolecular chemistry·2025
Same author

In silico structure revision of zerumol A.

Fitoterapia·2025
Same author

Crotonguaienone G and pernambucone are identical.

Fitoterapia·2025
Same author

Peganutonin A: Computationally Informed Synthesis of Its Revised Structure.

Journal of natural products·2025

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Heterocyclic Chemistry

Background:

  • O-homoallylhydroxylamines are versatile precursors in organic synthesis.
  • Palladium and copper catalysis offer efficient routes to complex molecules.
  • Isooxazolidines are important heterocyclic compounds with various applications.

Purpose of the Study:

  • To develop a novel synthetic method for isooxazolidines.
  • To investigate the role of catalyst systems (palladium(II) and copper(II)) in the reaction.
  • To explore the influence of substituents on the hydroxylamine nitrogen.

Main Methods:

  • Treatment of O-homoallylhydroxylamines with palladium(II) and copper(II) catalysts.
  • Reaction conducted in the presence of a base, methanol, and carbon monoxide.

Related Experiment Videos

  • Utilizing electron-withdrawing groups, specifically carbamates, on the hydroxylamine nitrogen.

    • Main Results:

    • Successful formation of isooxazolidines from O-homoallylhydroxylamines.
    • Demonstrated the necessity of an electron-withdrawing group on the hydroxylamine nitrogen.
    • Observed exclusive formation of cis isomers when carbamate groups were employed.

    Conclusions:

    • A new palladium- and copper-catalyzed carbonylation reaction provides access to isooxazolidines.
    • Electron-withdrawing groups on the nitrogen are essential for this cyclization.
    • Carbamate-protected hydroxylamines yield stereoselective cis-isooxazolidines.