Indenes are utilised as building blocks in organic syntheses, and they often appear as the key structural motif in many natural products with interesting biological activities and in functional materials. For these reasons, the construction of an indene ring system has become a hot topic of interest for chemists. To date, a variety of synthetic methods to facilitate the formation of an indene ring have been reported. Although transition-metal catalysis are widely used in the synthesis of a wide range of different substituted indenes, there are still important regioselectivity issues concerning multi-substituted indene derivatives that need to be addressed. Here, we have demonstrated a highly regiospecific fashion for the synthesis of 1H-indene-2-carbaldehyde derivatives through transition-metal-free, cascade reductive cyclisation of ortho-formyl trans-cinnaldehydes with Hantzsch ester in the presence of an aminocatalyst. Especially, cycloolefin isomerisation of the resulting products could be inhibited efficiently by the introduction of a sterically demanding stereo-defined aminocatalyst.