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

Spiro-cyclopropanation from oxoallylsilanes.

Asunción Barbero1, Pilar Castreño, Francisco J Pulido

  • 1Departamento de Química Orgánica, Universidad de Valladolid, 47011 Valladolid, Spain.

Journal of the American Chemical Society
|June 2, 2005
PubMed
Summary

A new spiro-cyclopropanation reaction using oxoallylsilanes creates complex polycyclic molecules. This stereoselective method offers a novel pathway to synthesize unique hydroxylated structures with spiro-cyclopropane units.

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

Organosilicon molecules bind to the intrinsically disordered protein NUPR1 by clamping its hot-spots.

Archives of biochemistry and biophysics·2025
Same author

Terminal Cyclopropylsilyl Alcohols as Useful Key Units to Access 2,3,4,6-Tetrasubstituted Tetrahydropyran Scaffolds by Stereocontrolled Prins Cyclization.

Organic letters·2024
Same author

Towards an efficient methodology for the synthesis of functionalized dihydropyrans by silyl-Prins cyclization: access to truncated natural products.

RSC advances·2024
Same author

Continuous Flow Chemistry: A Novel Technology for the Synthesis of Marine Drugs.

Marine drugs·2023
Same author

Therapeutic Potential of Heterocyclic Compounds Targeting Mitochondrial Calcium Homeostasis and Signaling in Alzheimer's Disease and Parkinson's Disease.

Antioxidants (Basel, Switzerland)·2023
Same author

Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound.

The Journal of organic chemistry·2023

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Stereoselective Synthesis

Background:

  • Oxoallylsilanes are versatile synthetic intermediates.
  • Spiro-cyclopropane motifs are present in various natural products and pharmaceuticals.
  • Efficient methods for constructing spiro-cyclopropane systems are highly sought after.

Purpose of the Study:

  • To develop a novel, highly stereoselective spiro-cyclopropanation reaction.
  • To synthesize hydroxylated polycyclic systems featuring a spiro-cyclopropane moiety.
  • To explore the scope and mechanism of the developed reaction.

Main Methods:

  • Preparation of oxoallylsilanes via silylcupration of allene and conjugate addition to enones.
  • Tandem cyclization-cyclopropanation reaction using diiodomethane (CH2I2) and trimethylaluminum (Me3Al).

Related Experiment Videos

  • Analysis of reaction scope and mechanistic investigation.

    • Main Results:

    • A novel, highly stereoselective spiro-cyclopropanation of oxoallylsilanes was achieved.
    • The reaction provides access to hydroxylated polycyclic systems containing the spiro-cyclopropane unit.
    • The scope of the reaction was investigated, demonstrating its utility.

    Conclusions:

    • A new synthetic route to complex spiro-cyclopropane-containing molecules has been established.
    • The developed method offers a valuable tool for organic synthesis.
    • The reaction proceeds through a tandem cyclization-cyclopropanation pathway.