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Palladium-Catalyzed Asymmetric Allylic Cycloaddition of Vinylethylene Carbonates with Nitroalkenes: A Route to Tetrahydrofurans bearing Vicinal Tetrasubstituted Stereocenters

  • Can Zhao
  • , Sardaraz Khan
  • , Ijaz Khan
  • , Babar Hussain Shah
  • , Yong Jian Zhang*
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

An efficient method for the diastereo- and enantioselective construction of tetrahydrofurans bearing three continuous stereocenters including vicinal tetrasubstituted stereocenters via palladium-catalyzed asymmetric allylic cycloaddition of vinylethylene carbonates with nitroalkenes was developed. By using a palladium complex generated in situ from [Pd2(dba)3] ⋅ CHCl3 and (R)-BINAP ligand as a catalyst under mild reaction conditions, the process provides multi-functionalized tetrahydrofurans in good yields with excellent stereoselectivities.

Original languageEnglish
Article numbere202200313
JournalAsian Journal of Organic Chemistry
Volume11
Issue number8
DOIs
StatePublished - Aug 2022
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

  • allylic cycloaddition
  • asymmetric catalysis
  • multi-substituted tetrahydrofurans
  • palladium-catalyzed reaction
  • quaternary stereocenters

ASJC Scopus subject areas

  • Organic Chemistry

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