Earth-Abundant-Metal-Catalyzed Asymmetric Hydrofunctionalizations of Alkenes with Acid Derivatives

Abstract Chiral carbonyl compounds featuring α-stereocenters represent a fundamental structural motif prevalent in natural products and pharmaceutically relevant molecules. While transition-metal-catalyzed asymmetric hydrofunctionalization of alkenes offers a direct route to these scaffolds, established protocols typically rely on precious metals and toxic carbon monoxide gas. To address these challenges, this review highlights recent advancements in earth-abundant-metal-catalyzed asymmetric hydrofunctionalizations of alkenes utilizing acid derivatives as stable electrophilic coupling partners. We specifically focus on copper- and nickel-catalyzed strategies that employ reagents such as acid anhydrides, chloroformates, and carbamoyl chlorides to achieve enantioselective hydroacylation, hydrocarboxylation, and hydrocarbamoylation. These emerging protocols not only operate under mild conditions but also offer complementary chemo- and regioselectivity, enabling the efficient synthesis of structurally diverse α-chiral ketones, esters, and amides.