Applications. To demonstrate the potential of enantioselective oxidative coupling reaction in organic synthesis, we applied our method to the derivatization of bioactive molecules, which is a commonly used strategy for drug discovery (Fig. ). Medicines containing a carboxylic acid group, such as ibuprofen, naproxen, probenecid, and gemfibrozil, reacted with (E)-but-1-en-1-ylbenzene to produce the corresponding allyl esters (3ao-3ar) with high diastereoselectivity or enantioselectivity. The natural product ursolic acid has three allyl sites, and only one site (3as and 3at) reacts with p-methoxybenzoic acid, showing an excellent site-selectivity. The alkynes derived from tigogenin (5w) and dihydrocholesteol (5x) can be coupled with acid to form propargyl C-H bond oxidation products with high enantioselectivity. These examples underscored the high efficiency of the enantioselective oxidative coupling of C(sp 3 )-H bonds with carboxylic acids-the direct synthesis of chiral esters from alkenes and alkynes-and their broad applicability in bioactive molecule synthesis and drug discovery.