Synthesis of Some Novel Amino Phenols with Octahydro-1,1′-binaphthyl Backbone^†

A series of new octahydro-1,1′-binaphthyl derivatives, namely (R)-(+)-2-(N, N-dialkylamino)-2′-hydroxy-5,5′,6,6′,7, 7′,8,8′-octahydro-1,1′-binaphthyls (7,9), have been synthesized. Their asymmetric induction for enantioselective addition of Et₂Zn to benzaldehyde was examined and it was found that (R)-(+)-2-(N-cyclohexyl-N-methylamino)-2′-hydroxy-5, 5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl (9c) exhibited the best asymmetric induction among the ligands prepared, up to 55% ee of 1-phenylpropanol being obtained.