Palladium-catalyzed diastereo- and enantioselective desymmetric hydrophosphination of cyclopropenes

Yiliang Zhang, Yanxin Jiang, Mingliang Li, Zhongxing Huang, Jun (Joelle) Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Cyclopropanes are unique three-member rings whose unusual bonding and inherent ring strain make them valuable building blocks in modern organic synthesis. In this work, a Pd-catalyzed diastereo- and enantioselective desymmetric hydrophosphination of 3,3-disubstituted cyclopropenes is described. It allows efficient, direct, and atom-economic access to potentially valuable chiral cyclopropane rings bearing two vicinal carbon stereocenters in high yields with excellent diastereo- and enantioselectivities (up to >98:2 d.r. [diastereomeric excess] and 97% ee [enantiometric excess]). Further transformations of these chiral phosphorus-containing three-member rings provide a range of potential applications.

Original languageEnglish
Pages (from-to)3163-3173
Number of pages11
JournalChem Catalysis
Volume2
Issue number11
DOIs
Publication statusPublished - 17 Nov 2022

Scopus Subject Areas

  • Chemistry (miscellaneous)
  • Physical and Theoretical Chemistry
  • Organic Chemistry

User-Defined Keywords

  • cyclopropane
  • C–P bond formation
  • desymmetric
  • hydrophosphination
  • palladium

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