Palladium-catalyzed synthesis of a phosphine oxide with a chiral phosphorus center via C-H phosphination

Yoichiro Kuninobu, Kazuki Origuchi, Kazuhiko Takai

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A new phosphine oxide with a chiral phosphine center was synthesized from a bis(biphenyl)phosphine oxide by dehydrogenative intramolecular cyclization via P-H and C-H bond activation under palladium catalysis. The absolute configuration of one enantiomer of the phosphine oxide was determined by single crystal X-ray structure analysis. By reducing the phosphine oxide, the corresponding phosphine, which also has a chiral center, was produced. The phosphine compounds could be optically resolved by chiral HPLC column chromatography.

Original languageEnglish
Pages (from-to)3029-3034
Number of pages6
JournalHeterocycles
Volume85
Issue number12
DOIs
Publication statusPublished - 2012

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phosphine
Palladium
Phosphorus
Oxides
Column chromatography
Enantiomers
Cyclization
Catalysis
Chromatography

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Palladium-catalyzed synthesis of a phosphine oxide with a chiral phosphorus center via C-H phosphination. / Kuninobu, Yoichiro; Origuchi, Kazuki; Takai, Kazuhiko.

In: Heterocycles, Vol. 85, No. 12, 2012, p. 3029-3034.

Research output: Contribution to journalArticle

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