PPFA

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.

C26H28FeNP_1

Palladium

Pd – Asymmetric Suzuki cross-coupling CC00-1723 and Tet04-60-4377

PN-L2_Pd_CC00-1723

CEJ06-12-9346

PN-L2_Pd_CEJ06-12-9346

 

Pd – Asymmetric Negishi cross-coupling TA06-17-2593

PN-L2_Pd_TA06-17-2593

BCSJ83-56-363

PN-L2_Pd_BCSJ83-56-363

Pd – Asymmetric Grignard cross-coupling JOC86-51-3772

PN-L2_Pd_JOC86-51-3772

 

Pd – Asymmetric organoindium cross-coupling EJOC13-2555

PN-L2_Pd_EJOC13-2555

 

Copper

Cu – 3 + 2 cycloaddition JACS07-129-750

PN-L2_Ag_JACS07-129-750

Not an example of >80% ee but included as the corresponding  ligand with NMereplaced by NHresults in a hydrogen-bonding reversal of enantioselectivity (83% ee).

 

Cu – Imine alkylation TA05-16-2531

PN-L2_Cu_TA05-16-2531

 

Cu – Conjugate addition TA06-17-136

PN-L2_Cu_TA06-17-136

Absolute configuration of products assigned by use of data in TA12-23-130