A WIDELY APPLICABLE CHIRAL AUXILIARY, CIS-2-AMINO-3,3-DIMETHYL-1-INDANOL - CONVERSION TO A NOVEL PHOSPHORUS-CONTAINING OXAZOLINE AND ITS APPLICATION AS A HIGHLY EFFICIENT LIGAND FOR THE PALLADIUM-CATALYZED ENANTIOSELECTIVE ALLYLIC AMINATION REACTION

A chiral amino alcohol, cis-2-amino-3,3-dimethyl-1-indanol (2), was co nverted into the corresponding enantiomerically pure phosphorus-contai ning oxazoline 4. Oxazoline 4 was found to be an efficient ligand for palladium-catalyzed enantioselective allylic amination reactions: In t he amination reaction of (E)-1,3-diphenyl-2-propen-1-yl acetate (7a), 4 was found to be more efficient than the similar ligands 1a-c, derive d from valinol, tert-leucinol, etc. Other 1,3-bis(p-substituted aryl)- 2-propen-1-yl acetates were also converted to the corresponding amines in a similar manner and with excellent enantioselectivity. In the ami nation reaction of 1-alkyl-3,3-diphenyl-2-propen-1-yl acetates 11, the correponding amines 12 were obtained with excellent enantioselectivit y when acetic acid was added to the reaction system.