Expanding the Utility of Lithiated Epoxides and Aziridines in Synthesis

1 Introduction 2 Epoxides and Organolithiums 2.1 Enantioselective Desymmetrisation of meso-Epoxides by (alpha)-Lithiation-Rearrangement 2.2 Reductive Alkylation of Epoxides with Organolithiums 2.3 (alpha)-Lithiated Epoxides of Cycloalkenes as Nucleophiles 2.4 (alpha)-Lithiated Terminal Epoxides as Nucleophiles 3 Terminal Epoxides and Lithium Amides 3.1 Electrophile Trapping 3.2 Enamines from Epoxides and Hindered Lithium Amides 3.3 Intramolecular Cyclopropanation 3.4 Reductive Alkylation in the presence of LTMP 3.5 Dimerisation of (alpha)-Lithiated Epoxides 4 (alpha)-Lithiated Aziridines 4.1 Reductive Alkylation of Aziridines with Organolithiums 4.2 (alpha)-Lithiated Terminal Aziridines as Nucleophiles 5 Summary and Outlook