The asymmetric Pictect-Spengler reaction (PSR) between tryptamine and aldehydes is now well-developed. Conversely, catalytic enantioselective PSR of ketone is essentially unexploited. In this presentation, we will present our work on the catalytic enantioselective PSR of tryptamine with 1,2-diones, α-ketoesters and α-ketoamide for the synthesis of enantioenriched 1,1-disubstituted tetrahydro-α-carboline (THBC) and their application in the total synthesis of monoterpene indole alkaloids.