We also observed single diastereomer of the product by 1 H, and C NMR. Then we tried different combinations of solvent with HFIP but there was no any improvement in the yield or reaction time (Table , entry 9-11). With optimized solvent in hand, we checked effect of catalyst, we carried out reaction without 10% Pd/C and observed that there was no product formation (Table , entry 12). Furthermore, we checked the reaction without an H2 atmosphere and there was no product formation ( With the optimized reaction condition in hand, we focus to exploration of the substrate scope which proves the efficiency of reaction in presence of different functional groups. First, we tested indolylidenecyanoacetates with electron donating groups like, 5-Me, 5-Ome, we observed that these group are well tolerated during the course of reaction and delivered high yield of required product 4Ab and 4Ac with only one diastereomer. In addition, multi-substituted indolylidenecyanoacetates like, 5,7-Dimethyl substrate also gave high yield of corresponding product with only one diastereomer 4Ad. Then, we explored halogen group at different position to check tolerance of halogen group in the reaction. With halogen group at different position like, 5-F and 7-F indolylidenecyanoacetates both the substrates furnished the corresponding product with good yield and only one diastereomer 4Ae and 4Af. Unfortunately, in case of 4-Cl, 5-Cl, 7-Cl, 5-Br, 6-Br substituted indolylidenecyanoacetates, did not offer corresponding products, instead of required product it gave dehalogenated product 4Aa in all cases. Further we tried methodology for substrates containing electron withdrawing groups like 5-OCF3, which gave the corresponding product with good yield 4Ag. Furthermore, we tried substrate with more electron withdrawing groups like 7-CF3 and 5-NO2 but reaction is not procced for first step (nitro-Michael reaction) possibly due to high acidic free N-H group present in substrate that quench organic catalyst. Then we check reaction with Nmethyl protected substrates with 7-CF3 which gave good yield of product 4Ah. Further we checked for N-methyl protected 5-NO2 substrates which delivered corresponding product with reduction of 5-NO2 to 5-NH2 group 4Ai.