Abstract
This account details new reactions and synthetic uses of lithiated epoxides and aziridines that have been developed in the principal author’s laboratories.
1 Introduction
2 Epoxides and Organolithiums
2.1 Enantioselective Desymmetrisation of meso -Epoxides by α-Lithiation-Rearrangement
2.2 Reductive Alkylation of Epoxides with Organolithiums
2.3 α-Lithiated Epoxides of Cycloalkenes as Nucleophiles
2.4 α-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 α-Lithiated Epoxides
4 α-Lithiated Aziridines
4.1 Reductive Alkylation of Aziridines with Organolithiums
4.2 α-Lithiated Terminal Aziridines as Nucleophiles
5 Summary and Outlook
Key words
asymmetric synthesis - aziridines - carbenoids - epoxides - lithiation
References and Notes 1 Present address: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
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