Lithiation-Induced Migrations from Nitrogen to Carbon in Terminal Aziridines


  • We thank the EPSRC and GlaxoSmithKline for a CASE award (to P.G.H.), the Royal Society for an International Incoming Fellowship (to Z.X.), the EPSRC National Mass Spectrometry Service (Swansea) for mass spectra, S. P. Hughes for preliminary observations, and Prof. W. Clegg and Dr. L. Russo (University of Newcastle) for GSK-funded X-ray crystallographic analysis.


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Benefiting from deprotection: Lithium 2,2,6,6-tetramethylpiperidide induces N-Boc or N-phosphonate terminal aziridines to undergo regio- and stereoselective N-to-C migration of the protecting group, giving synthetically valuable trans-aziridinylesters and trans-aziridinylphosphonates.