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

Jens Holz; Haijun Jiao; Mark Gandelman; Armin Börner

doi:10.1002/ejoc.201701734

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

Jens Holz, Haijun Jiao, Mark Gandelman, Armin Börner

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

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 language	English
Pages (from-to)	2984-2994
Number of pages	11
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	23
DOIs	https://doi.org/10.1002/ejoc.201701734
State	Published - 22 Jun 2018
Externally published	Yes

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

Keywords

Chiral resolution
Chirality
Inversion barrier
Isomerization
P ligands
Phosphanes
Racemization

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KW - Inversion barrier

KW - Isomerization

KW - P ligands

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KW - Racemization

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

Abstract

Bibliographical note

Keywords

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