882525-50-0Relevant articles and documents
Dimerization of lithiated terminal aziridines
Hodgson, David M.,Miles, Steven M.
, p. 935 - 938 (2006)
Let's get together: Dimerization of enantiopure terminal aziridines by lithiation gives efficiently N-protected 2-ene-1,4-diamines with complete selectivity for the E olefin (see scheme). The usefulness of the method was demonstrated in a concise synthesis of (R,S,S,R)-2,5-diamino-1,6-diphenylhexane- 3,4-diol, the core unit of many extremely potent HIV protease inhibitors and also asymmetric catalysts. (Chemical Equation Presented).
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.
