We aim at developing a general strategy for the production of highly enantioenriched aldehydes and amines through desymmetrization of prochiral C-H bonds using palladium catalysis. The catalytic and enantioselective functionalization of prochiral unactivated C–H bonds offers great opportunity in the production of a broad range of enantioenriched compounds. Accordingly, various elegant catalysis concepts have been developed to achieve enantioselective functionalization of C-H bond. Among them, the directing group assisted C−H bond activation via metal insertion has been extensively studied using modified substrates and chiral ligand. While numerous enantioselective C-H bond functionalizations have already been reported with this strategy, it however requires the covalent installation of a suitable directing group into the substrates, which remains a major drawback of this process. To address current limitation of the process, the use of transient directing group (TDG) in C-H functionalization reaction emerges as an effective alternative. Accordingly, efforts have been given in designing and developing new catalytic reaction utilizing the concept of TDG. Despite these reports, the development of catalytic enantioselective C–H functionalization reaction using chiral TDG is relatively less explored. We intend to examine different chiral amino acid derivatives or chiral α/β hydroxyl aldehydes as chiral TDGs for the desymmetrization of aldehyde and amines, respectively. The TDGs are expected to serve as directing group and as the source of chirality for the proposed Pd-catalyzed desymmetrization reactions.