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

Enantioenriched dihydropyrones from beta-lactone templates.

G Greg Zipp1, Mark A Hilfiker, Scott G Nelson

  • 1Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

Organic Letters
|May 25, 2002
PubMed
Summary
This summary is machine-generated.

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

Identifying general reaction conditions by bandit optimization.

Nature·2024
Same author

Discovery of GSK2798745: A Clinical Candidate for Inhibition of Transient Receptor Potential Vanilloid 4 (TRPV4).

ACS medicinal chemistry letters·2019
Same author

Reverse Hydroxamate Inhibitors of Bone Morphogenetic Protein 1.

ACS medicinal chemistry letters·2018
Same author

Reaction profiling by ultra high-pressure liquid chromatography/time-of-flight mass spectrometry in support of the synthesis of DNA-encoded libraries.

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences·2014
Same author

Novel inhibitors of the high-affinity L-proline transporter as potential therapeutic agents for the treatment of cognitive disorders.

Bioorganic & medicinal chemistry letters·2014
Same author

Optimization of a Novel Series of TRPV4 Antagonists with In Vivo Activity in a Model of Pulmonary Edema.

ACS medicinal chemistry letters·2014

Optically active beta-lactones serve as precursors for synthesizing enantioenriched dihydropyrones. This study details a method using asymmetric catalysis and hydrazone anion-mediated reactions for efficient heterocycle preparation.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Heterocyclic Chemistry

Background:

  • Optically active 4-substituted 2-oxetanones (beta-lactones) are valuable synthetic intermediates.
  • Enantioselective synthesis of beta-lactones is crucial for accessing chiral molecules.

Purpose of the Study:

  • To develop an efficient method for preparing enantioenriched 2,3-dihydro-4H-pyrones.
  • To utilize optically active beta-lactones as precursors in heterocyclic synthesis.

Main Methods:

  • Asymmetric catalytic acyl halide-aldehyde cyclocondensation for beta-lactone synthesis.
  • Hydrazone anion-mediated ring opening of beta-lactones.
  • Cyclization-dehydroamination of beta-ketohydrazones.

Main Results:

Related Experiment Videos

  • Successful synthesis of enantioenriched 2,3-dihydro-4H-pyrones from optically active 4-substituted 2-oxetanones.
  • Yields for the dihydropyrone formation ranged from 68-81%.
  • Optimized reaction conditions demonstrated the versatility of the method.

Conclusions:

  • Optically active beta-lactones are effective precursors for enantioenriched dihydropyrones.
  • The developed synthetic route provides a reliable pathway to these important heterocycles.
  • This methodology expands the toolkit for asymmetric synthesis of chiral compounds.