726138-80-3Relevant academic research and scientific papers
Persistent N-chirality as the only Source of asymmetry in nonracemic N 2PdCl2 complexes
Pelz, Kathryn A.,White, Peter S.,Gagne, Michel R.
, p. 3210 - 3217 (2008/10/09)
The combination of prochiral 1,2-diamines, Pd(OAc)2, and (R)-K2-3,3′-Me2BINOL leads to enantio- and diastereopure N2Pd(3,3′-Me2BINOL) complexes. HCl removes the Me2BINOL resolving ligand and provides a family of enantiopure N2PdCl2 complexes whose only stereochemistry resides on the stereogenic nitrogen centers. In effect, nitrogen inversion (>105 s-1) is halted by metal coordination and utilized to generate enantiopure complexes. When the diamine substituents are relatively small, the N-chirality is stable; however, large substituents accelerate N-dissociation processes and concomitant racemization. Enantiopure N 2Pd2+-Lewis acid catalysts can be generated for the Diels-Alder reaction, and although enantioselectivities are low (a degradation of the catalyst's chirality.
