Supramolecular hydrogen-bonding tautomeric sulfonamido-phosphinamides: A perfect p-chirogenic memory

Frederic W. Patureau, Maxime A. Siegler, Anthony L. Spek, Albertus J. Sandee, Sylvain Jugé, Sarwar Aziz, Albrecht Berkessel, Joost N.H. Reek

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16 Scopus citations


P-chirogenic, supramolecular hydrogen-bonding C1-symmetrical sulfonamido-phosphinamides (METAMORPhos) have been successfully prepared. They were all found to possess a characteristic prototropic equilibrium between the PIII and the PV tautomers that is slow on the NMR spectroscopic timescale. Despite the dynamic and reversible protonation of the P centre, the P-chirogenic information was found to be retained in the tautomerization process, even in a protic solvent environment. Several strategies to access the corresponding enantiopure compounds were investigated, such as diastereoselective crystallization, or enantioselective synthesis. It was possible to resolve such a class of chiral ligands with up to 99 % ee, and apply them in the Rh-catalyzed asymmetric hydrogenation of alkenes. These ligands are interesting new building blocks in the area of acid/base-type noninnocent ligand catalysis.

Original languageEnglish
Pages (from-to)496-503
Number of pages8
JournalEuropean Journal of Inorganic Chemistry
Issue number3
StatePublished - Jan 2012
Externally publishedYes


  • Chirality
  • Hydrogenation
  • Phosphorus
  • Rhodium
  • Tautomerism


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