The asymmetric synthesis of cis-1,4-amino alcohols with a norbornene backbone was performed starting with (2S,3R)-(−)-cis-hemiester 2 (98% ee). Chemoselective amination with NH 4 OH and HMPTA followed by LAH reduction afforded 5 and 7, respectively. Amido ester 6 was transformed into chiral ligand 9 with Grignard reaction followed by LAH reduction. The chiral ligands 5, 7, and 9 were subjected to asymmetric diethylzinc addition to examine their effectiveness as chiral catalysts. Among these, chiral ligand 7 exhibited the highest enantioselectivity (88% ee).