Organocatalyzed and metal complex-catalyzed asymmetric decarboxylative aldol reactions of malonic acid half thioesters (MAHTs), malonic acid half oxyester (MAHOs), and β-ketoacids with different carbonyl compounds are transformations of high synthetic value. These reactions, which are heavily inspired by nature's synthesis strategies, represent important methods for the direct synthesis of valuable enantio-enriched β-hydroxy esters and ketones. Within this short review we wish to give an overview about the recent progress in this field by discussing the leading strategies to carry out decarboxylative aldol reactions using organocatalytic methods as well as metal catalysis.