The development of palladium-catalyzed carboetherification and carboamination reactions between aryl or alkenyl halides and alkenes bearing pendant heteroatoms is described. These transformations effect the stereoselective construction of useful heterocycles, such as tetrahydrofurans, pyrrolidines, imidazolidin-2-ones, isoxazolidines, and piperazines. The scope, limitations, and applications of these reactions are presented, and current stereochemical models are described. The mechanism of the product formation, which involves an unusual intramolecular syn-insertion of an alkene into a palladium-heteroatom bond, is also discussed in detail. 1 Introduction 2 Palladium-Catalyzed Synthesis of Tetrahydrofurans from γ-Hydroxyalkenes and Aryl or Alkenyl Halides 2.1 Mechanism of the Tetrahydrofuran Formation 3 Palladium-Catalyzed Synthesis of Pyrrolidines from γ-Aminoalkenes and Aryl or Alkenyl Halides 3.1 Tandem Palladium-Catalyzed N-Arylation-Carboamination Reactions of Primary Amines 3.2 Palladium-Catalyzed Carboamination Reactions of N-Protected γ-Aminoalkenes 3.3 Mechanism of the Palladium-Catalyzed Carboamination Reactions: Surprises and Utility 3.4 Application of the Palladium-Catalyzed Carboamination of N-Protected γ-Aminoalkenes to the Stereoselective Synthesis of (+)-Preussin and Its Analogues 4 Synthesis of Imidazolidin-2-ones via Palladium-Catalyzed Carboamination Reactions 5 Synthesis of Isoxazolidines via Palladium-Catalyzed Carboetherification Reactions 6 Synthesis of Piperazines via Palladium-Catalyzed Carboamination Reactions 7 Summary and Future Outlook