Skip to content
DraconiticResearch
Search Sources API
203,234 studies31 sourcesUpdated 50 min ago
PreprintCC BYChemRxiv

Pd-catalyzed Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Diastereo- and Enantioselective Access to Spirooxindoles

  • Xavier Xancho1,2
  • Pinar Yildirim1,2
  • Nicolas Casaretto3,4
  • Alexis Archambeau
4 affiliations
  1. 1Laboratoire de Synthèse Organique
  2. 2UMR 7652, CNRS, Ecole Polytechnique, ENSTA Paris, Institut Polytechnique de Paris
  3. 3Laboratoire de Chimie Moléculaire, UMR 9168, CNRS, Ecole Polytechnique
  4. 4Institut Polytechnique de Paris
Open at sourcePDFDOICite

Abstract

In this manuscript, we report a straightforward route to spirooxindoles by Pd-catalyzed cycloadditions of 5-vinyloxazolidine-2,4-diones with isatins. After a screening of chiral ligands, DTBM-SEGPHOS was selected to induce high diastereo- and enantiocontrol of the two newly created tetrasubstituted stereocenters. Our investigation demonstrated broad functional group tolerance under the reaction conditions. Overall, this work represents a rare example of Pd-catalyzed cycloadditions involving 5- vinyloxazolidine-2,4-diones and electrophilic C=O bonds.

Related

  1. Nickel-Catalyzed Formal [3+2+2] Cycloadditions of Bis(trimethylsilyl)cyclopropanone withDiynes: A Concise Approach to Functionalized Azulene Derivatives
    Yuki Sato, Sayaka Ohrui, Masanori Tayu +6
    ChemRxivPreprintCC BYFull textOrganic chemistryChemRxiv
  2. Enantioselective cobalt-catalyzed intermolecular [3+2] cycloaddition of cyclopropenes with terminal alkynes to access chiral cyclopentadienes
    Bin Yang, Shaozhong Ge
    Nature CommunicationsPeer-reviewedCC BY-NC-ND 4.0Full textOrganic chemistryCrossref
  3. Convergent Approach for the Asymmetric Synthesis of Vinyl Sulfoximines via Ruthenium-Catalyzed Enantioselective Alkylation of Sulfenamides with (Diazomethyl)phosphonates
    Zachary W. Boyer, Christopher W. Smith, Jonathan A. Ellman
    Organic lettersPeer-reviewedLicence not statedFull textOrganic chemistryPMC
  4. A dynamically tunable diamine ligand enables Cu-catalyzed enantioselective nucleophilic substitution at P(V)
    Jie Wei, Kai Tang, Shuai-Shuai Fang +5
    Nature CommunicationsPeer-reviewedCC BY-NC-ND 4.0Full textOrganic chemistryCrossref
  5. Enantioselective Formal Synthesis of (-)-Neoxaline Enabled by an Asymmetric Ir-Catalyzed Reverse Prenylation.
    Jonathan Farhi, Brian M Stoltz
    The Journal of organic chemistryPeer-reviewedCC BY-NC-NDFull textOrganic chemistryEurope PMC

Cite

BibTeXRIS
BibTeX
@misc{xancho2026pdcatalyzed,
  title = {{Pd-catalyzed Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Diastereo- and Enantioselective Access to Spirooxindoles}},
  author = {Xavier Xancho and Pinar Yildirim and Nicolas Casaretto and Alexis Archambeau},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010174/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010174/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Pd-catalyzed Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Diastereo- and Enantioselective Access to Spirooxindoles
AU  - Xavier Xancho
AU  - Pinar Yildirim
AU  - Nicolas Casaretto
AU  - Alexis Archambeau
PY  - 2026
DA  - 2026/10/09
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010174/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010174/v1
AB  - In this manuscript, we report a straightforward route to spirooxindoles by Pd-catalyzed cycloadditions of 5-vinyloxazolidine-2,4-diones with isatins. After a screening of chiral ligands, DTBM-SEGPHOS was selected to induce high diastereo- and enantiocontrol of the two newly created tetrasubstituted stereocenters. Our investigation demonstrated broad functional group tolerance under the reaction conditions. Overall, this work represents a rare example of Pd-catalyzed cycloadditions involving 5- vinyloxazolidine-2,4-diones and electrophilic C=O bonds.
ER  -