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 converted into the corresponding enantiomerically pure phosphorus-containing oxazoline 4 . Oxazoline 4 was found to be an efficient ligand for palladium-catalyzed enantioselective allylic amination reactions: In the 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, derived 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 amination reaction of 1-alkyl-3,3-diphenyl-2-propen-1-yl acetates 11, the correponding amines 12 were obtained with excellent enantioselectivity when acetic acid was added to the reaction system.