881840-76-2Relevant academic research and scientific papers
Dimerization and isomerization reactions of α-lithiated terminal aziridines
Hodgson, David M.,Humphreys, Philip G.,Miles, Steven M.,Brierley, Christopher A. J.,Ward, John G.
, p. 10009 - 10021 (2008/03/28)
(Chemical Equation Presented) The scope of dimerization and isomerization reactions of α-lithiated terminal aziridines is detailed. Regio-and stereoselective deprotonation of simple terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide (LTMP) or lithium dicyclohexylamide (LiNCy 2) generates trans-α-lithiated terminal aziridines. These latter species can then undergo dimerization or isomerization reactions depending on the nature of the N-protecting group. α-Lithiated terminal aziridines bearing N-alkoxycarbonyl (Boc) protection undergo N- to C-[1,2] migration to give N-H trans-aziridinylesters. In contrast, aziridines bearing N-organosulfonyl [tert-butylsulfonyl (Bus)] protection undergo rapid dimerization to give 2-ene-1,4-diamines or, if a pendant alkene is present, diastereoselective cyclopropanation to give 2-aminobicyclo[3.1.0]hexanes. All of these reactions were used as key steps in the preparation of synthetically and biologically important targets.
Intramolecular cyclopropanation of unsaturated terminal aziridines
Hodgson, David M.,Humphreys, Philip G.,Ward, John G.
, p. 995 - 998 (2007/10/03)
Regio- and stereoselective deprotonation of bishomoallylic terminal N-Bus (Bus = tert-butylsulfonyl)-protected aziridines generate aziridinyl anions that undergo diastereoselective Intramolecular cyclopropanation giving trans-2-aminobicyclo[3.1.0]hexanes in good to excellent yields.
