Synthesis of chiral nonracemic PC(sp3)P pincer ligands

•Synthesis of chiral enantiopure PCS pincer ligands is suggested.•The synthesized PCS ligand is chiral-at-frame.•Coordination chemistry of the new ligand was studied.

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.

Graphical abstractWe describe a straightforward synthetic route toward a new family of chiral nonracemic dibenzobarrelene-based pincer ligands.Figure optionsDownload full-size imageDownload as PowerPoint slide