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

Abstract

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-y] 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.