- Supramolecular hydrogen-bonding tautomeric sulfonamido-phosphinamides: a perfect P-chirogenic memory
- European Journal of Inorganic Chemistry
- Volume | Issue number
- 2012 | 3
- Pages (from-to)
- Document type
- Faculty of Science (FNWI)
- Van 't Hoff Institute for Molecular Sciences (HIMS)
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.
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