Asymmetric synthesis of Reissert compounds 5, 12 was achieved using chiral acyl halides such as amino acid fluorides or (-)-(R)-menthylchloroformate and TMSCN. These are the first cases of asymmetric synthesis of unsubstituted isoquinoline-derived Reissert compounds with high stereoselectivities. The chiral Reissert compound 12 could be alkylated in position 1 affording 1-substituted Reissert compound 13 highly stereoselectively. The products are potential starting materials for unnatural amino acids and alkaloid analogues.