Synthesis of C-2-symmetric analogues of 4-(pyrrolidino)pyridine: new chiral nucleophilic catalysts

The syntheses of a series of enantiomerically pure C-2-symmetric 4-(pyrrolidino)pyridine (PPY) derivatives by SNAr of 4-halo-/4-phenoxypyridines and by cyclocondensation from 4-aminopyridine are described. Preliminary results pertaining to their use as catalysts for acylative kinetic resolution of 1-phenylethanol are also presented. A single-crystal X-ray analysis of PPY If is reported.