About the Inversion Barriers of P-Chirogenic Triaryl-Substituted Phosphanes

Jens Holz, Haijun Jiao, Mark Gandelman, Armin Börner

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


The racemization tendency of acyclic P-chirogenic phosphanes is investigated experimentally and theoretically. Results of these investigations are important for the construction and use of P-chirogenic ligands and organocatalysts frequently used in asymmetric syntheses. Proof is given that triaryl phosphanes undergo easier racemization than compounds in which the phosphorus atom is linked to alkyl substituents. Interestingly, bulky ortho aryl substituents have only a marginal effect, whereas P-naphthyl rings destabilize the compound.

Original languageEnglish
Pages (from-to)2984-2994
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number23
StatePublished - 22 Jun 2018
Externally publishedYes

Bibliographical note

Funding Information:
We thank Mrs. Gudrun Wenzel for very skilled technical assistance. We acknowledge financial support by German-Israeli Foundation for Scientific Research and Development (GIF, Research Agreement Project no. I-1369-302.5/2016).

Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim


  • Chiral resolution
  • Chirality
  • Inversion barrier
  • Isomerization
  • P ligands
  • Phosphanes
  • Racemization


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