The original. First synthesised by Hayashi, Yamamoto and Kumada using the diastereoselective lithiation of N,N-dimethyl-1-ferrocenylethylamine reported previously by Ugi et al. PPFA has principally been employed as an intermediate in the synthesis of many other ligands, there being relatively few reports on the use of this as a ligand in asymmetric catalysis. Examples of Pd and Cu catalysis that result in >80% ee are listed below.
Pd – Asymmetric Negishi cross-coupling TA06-17-2593
Pd – Asymmetric Grignard cross-coupling JOC86-51-3772
Pd – Asymmetric organoindium cross-coupling EJOC13-2555
Cu – 3 + 2 cycloaddition JACS07-129-750
Not an example of >80% ee but included as the corresponding ligand with NMe2 replaced by NH2 results in a hydrogen-bonding reversal of enantioselectivity (83% ee).
Cu – Imine alkylation TA05-16-2531
Cu – Conjugate addition TA06-17-136
Absolute configuration of products assigned by use of data in TA12-23-130