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Abstract Enantioselective diamination of alkenes represents one of the most straightforward methods to access enantioenriched, vicinal diamines, which are not only frequently encountered in biologically active compounds, but also have broad applications in asymmetric synthesis. Although the analogous dihydroxylation of olefins is well-established, the development of enantioselective olefin diamination lags far behind. Nevertheless, several successful methods have been developed that operate by different reaction mechanisms, including a cycloaddition pathway, a two-electron redox pathway, and a radical pathway. This short review summarizes recent advances and identifies limitations, with the aim of inspiring further developments in this area. 1 Introduction 2 Cycloaddition Pathway 3 Two-Electron Redox Pathway 3.1 Pd(0)/Pd(II) Diamination 3.2 Pd(II)/Pd(IV) Diamination 3.3 I(I)/I(III) Diamination 3.4 Se(II)/Se(IV) Diamination 4 One-Electron Radical Pathway 4.1 Cu-Catalyzed Diamination 4.2 Fe-Catalyzed Diamination 5 Summary and Outlook