PURPOSE: To efficiently obtain the subject compound useful as a synthetic intermediate for medicines and agrochemicals, e.g. a synthetic intermediate for a tricyclic quinoxalinedione derivative which is a glutamic acid receptor antagonist by using an inexpensive raw material and utilizing an asymmetric chemical synthesis reaction.

CONSTITUTION: (A) Quinoline-2-acetic acid esters of formula I (R1 is H or a lower alkyl or a lower alkoxy; R2 is a lower alkyl) or (B) (Z)-2- alkoxycarbonylmethylidene 1,2,3,4 tetrahydroquinolines are subjected to asymmetric hydrogenation reaction using a metal complex having an asymmetric ligand as a catalyst to provide the objective optically active (2R)- or (2S)-1,2,3,4- tetrahydroquinoline-2-acetic esters of formula III or formula IV. For example, (2R)-1,2,3,4-tetrahydroquinoline-2-acetic acid methyl ester is obtained from quinoline-2 acetic acid methylester using a R-BINAP-ruthenium complex as the catalyst for the component C.