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Pure Appl. Chem., 2007, Vol. 79, No. 2, pp. 269-279

Widening the usefulness of epoxides and aziridines in synthesis

David M. Hodgson, Philip G. Humphreys and Steven P. Hughes

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK

Abstract: Deprotonation of terminal epoxides and aziridines with organolithium/diamine combinations or lithium amides allows the regio- and stereoselective formation of α-lithiated species. Judicious choice of reaction conditions allows these species to operate as nucleophiles, enolate equivalents, vinyl cation equivalents, or carbenes.