Supramolecular Hydrogen-Bonding Tautomeric Sulfonamido–Phosphinamides: A Perfect P-Chirogenic Memory

F.W. Patureau, M.A.M. Siegler, A.L. Spek, A. J. Sandee, S. Jugé, S. Aziz, A. Berkessel, J.N.H. Reek

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

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
Volume2012
Issue number3
DOIs
Publication statusPublished - 2012

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