Synthesis of chiral nonracemic PC(sp3)P pincer ligands

Orit Cohen, Olga Grossman, Luigi Vaccaro, Dmitri Gelman*

*Corresponding author for this work

Research output: Contribution to journalShort surveypeer-review

21 Scopus citations

Abstract

The manuscript describes a straightforward synthetic route toward a new family of chiral nonracemic dibenzobarrelene-based pincer ligands. The target molecules have been synthesized via lithiation of the racemic 1-bromo-8-diphenylphosphinotriptycene (2) and subsequent quenching with diastereomerically pure (1R,2S,5R)-(-)-menthyl (S)-p-toluenesulfinate. The resulting mixture of diastereomers was resolved using conventional column chromatography. Hydrogenation of the diastereomerically pure compounds lead to the formation of enantiopure PCS ligands.

Original languageAmerican English
Pages (from-to)13-16
Number of pages4
JournalJournal of Organometallic Chemistry
Volume750
DOIs
StatePublished - 2014

Bibliographical note

Funding Information:
This research was supported by the Israel Science Foundation. We especially thank Dr. Shmuel Cohen and Mr. Benny Bogoslavsky for solving X-ray structures.

Keywords

  • Chiral
  • Dibenzobarrelene
  • PC(sp3)P
  • Pincer complexes

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