The synthons containing sulfur and stereogenic phosphorus as heteroatoms: on the way to crystal structure determination of supramolecular complexes of organometallic and organic compounds

Abstract

The purpose of this study is to contribute to the process of establishing correlation between the three-dimensional structure of the chemical complex and enantiomeric yield of a stereospecific reaction. To achieve this goal, we synthesized, and will complexate with metal cations and organometallic moieties, the compounds which contain stereogenic heteroatom namely the optically active P-stereogenic phosphinic acid derivatives containing heavy atom such as sulfur. Our chiral thioacids, which we obtained in enantiomeric forms, are proposed to serve as new catalysts to replace the achiral copper acetate and palladium acetate, used routinely as catalysts in the reactions which require additional presence of another chiral ligand to assure the enantiomeric yield. Hereby we would like to present the progress on the X-ray structure determination of our synthesized series of thiophosphinic acids 1.

Graphical Abstract

Keywords:

• Chiral solvating agents
• thioacids
• thiophosphinic acids
• X-ray analysis
• absolute configuration
• conformation

Acknowledgments

CCDC depositions 1509139, 1589336, 1589363, and 1589364 contain the supplementary crystallographic data for Sp-1a, (bis)-Sp-1a disulfide, Rp-1b, and rac-1b, respectively. These data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/, or by e-mailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone].

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The authors thank for the support from the fund of the National Science Center awarded on the basis of the decisions UMO-2015/17/N/ST5/03908 (for JD).