Reaction SMILES: [CH3:1][O:2][CH2:3][C:4](=[C:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:13]1=O)[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C(=O)NC(=O)NC1=O.COC(OC)(C)C.[H][H].COCC(C1CCN(C(OCC2C=CC=CC=2)=O)C1=O)NC1C=CC=CC=1>CC(C)=O>[CH3:1][O:2][CH2:3][C@H:4]1[C@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C@H:13]2[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5]1
Reactant: [H][H]
Reactant: COCC(Nc1ccccc1)=C1CCN(C(=O)OCc2ccccc2)C1=O
Agent: COCC(Nc1ccccc1)C1CCN(C(=O)OCc2ccccc2)C1=O
Agent: O=c1[nH]c(=O)[nH]c(=O)[nH]1
Solvent: CC(C)=O
Solvent: COC(C)(C)OC
Product: COC[C@@H]1Nc2ccccc2[C@H]2[C@@H]1CCN2C(=O)OCc1ccccc1
Temperature: 25 °C
Reaction time: 1 h

Procedure:
Into a 10 mL Schlenk flask were charged [Rh(cod)2]OTf (19.2 mg) [mw. 468.34, 0.041 mmol, s/c 100] and (2S,4S)-skewphos (21.7 mg) [mw. 440.50, 6.6 μmol], and the system was substituted with argon. Deaeration-treated dehydrated acetone (5 mL) was added by argon pressure supply. Under an argon atmosphere, the mixture was stirred at room temperature for 1 hr. Separately, into a 120 mL stainless autoclave were charged benzyl 3-(2-methoxy-1-(phenylamino)ethylidene)-2-oxopyrrolidine-1-carboxylate (1.50 g) [mw. 366.41, 4.1 mmol] and cyanuric acid (0.53 g) [mw. 129.07, 4.1 mmol], and the system was substituted with argon. The catalyst in the Schlenk flask was added into the autoclave by argon pressure supply. Furthermore, dehydrated acetone (55 mL) and 2,2-dimethoxypropane (1.5 mL) [mw. 104.15, d=0.85, 12.3 mmol, 3.0 eq.] in the Schlenk flask was added into the autoclave by argon pressure supply. Hydrogen was filled therein to 5 MPa, and the mixture was stirred at a reaction temperature of 60° C. for 46 hr. The reaction mixture was cooled to room temperature and depressurized. Quantification by high performance liquid chromatography confirmed that the starting material, benzyl 3-(2-methoxy-1-(phenylamino)ethylidene)-2-oxopyrrolidine-1-carboxylate, remained by 27%, the reaction intermediate, benzyl 3-(2-methoxy-1-(phenylamino)ethyl)-2-oxopyrrolidine-1-carboxylate, remained by 35%, and the resultant product, (3aR,4R,9bR)-benzyl 4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-1-carboxylate, was produced by 34%. The optical purity of the resultant product was 60% ee. High performance liquid chromatography production rate analysis conditions: UV detector wavelength 220 nm, mobile phase 50 mmol/L aqueous potassium dihydrogen phosphate solution (adjusted to pH7.0 with 10% aqueous potassium hydroxide solution)/acetonitrile for high performance liquid chromatography=45/55, column YMC-Pack ODS-A A-302, measurement temperature 30° C., flow rate 1.0 mL/min. retention time benzyl 3-(2-methoxy-1-(phenylamino)ethyl)-2-oxopyrrolidine-1-carboxylate 6.9 min (reaction intermediate), (3aR,4R,9bR)-benzyl 4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-1-carboxylate 9.7 min (resultant product), benzyl 3-(2-methoxy-1-(phenylamino)ethylidene)-2-oxopyrrolidine-1-carboxylate 10.7 min (starting material). (This analysis method was used for Examples 36-40)