The progress in crystal structure determination of organometallic complexes and their organic synthons containing selenium and stereogenic phosphorus as heteroatoms

Abstract

The characterization of phosphines has attracted much attention in recent years because they are extensively used in asymmetric and stereoselective synthesis. In contrast to this, the P-stereogenic phosphinic acid derivatives which contain selenium, have been much less studied although they can be considered as useful stoichiometric and catalytic auxiliaries. For example, the enantiomeric tert-butylphenylphosphinoselenoic acids could be used as chiral solvating agents for the NMR determination of the enantiomeric excesses of a few optically active organic compounds with stereogenic carbon or heteroatoms. The progress on the X-ray structure determination of our synthesized selenophosphinic acids 1 is hereby presented. This should provide the three-dimensional architecture and verify proposed models of intramolecular interactions in supramolecular complexes with heteroorganic ligands. The acquired knowledge about supramolecular complex architecture and mechanism of action, will also be advantageous to synthetic chemists, to broaden the applicability of supramolecular compounds in stereocontrolled synthesis, for purpose to eliminate an expensive, time-consuming and non-stereoselective multi-step reaction protocols from use.

Graphical Abstract

Keywords:

• Chiral solvating agents
• selenoacids
• selenophosphinic acids
• X-ray analysis
• absolute configuration
• conformation

Acknowledgments

CCDC-1509140 contains the supplementary crystallographic data for Rp-1a. 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]. The authors thank for the support from the fund of the National Science Center Poland awarded on the basis of the decisions UMO-2015/17/N/ST5/03908 (for PPS).

Disclosure statement

No potential conflict of interest was reported by the authors.