Single or Synergistic Kinetic Resolutions of Chiral Allylalanes: Two Complementary Routes for the Asymmetric Synthesis of SynHomoallylamines

Two strategies based on kinetic resolution(s) of chiral alanes and providing enantioenriched synhomoallylamines are reported. The first implies a single kinetic resolution of the alane using camphor; the second requires two sequential kinetic resolutions using the synergistic combination of (−)-camphor/(R)-tert-butylsulfinamide-derived imines. This synselectivity, specific to the use of allyaluminum, opens the way to the preparation of valuable building blocks as illustrated by the synthesis of (+)-epilupinamine.