Abstract
AbstractP‐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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