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.
Keywords: asymmetric synthesis; aziridines; carbenoids; epoxides; lithiation.
*Paper based on a presentation at the 16th International Conference on Organic Synthesis (ICOS-16), 11-15 June 2006, Mérida, Yucatán, México. Other presentations are published in this issue, pp. 153-291.