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Synfacts 2008(11): 1207-1207
DOI: 10.1055/s-0028-1083463
DOI: 10.1055/s-0028-1083463
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereospecific α-Deprotonation of N-Protected Aziridines
S. P. Hughes, A. L. Thompson, T. D. Heightman, D. M. Hodgson*
University of Oxford, UK
Further Information
Publication History
Publication Date:
23 October 2008 (online)
Significance
A new method has been developed for α-lithiation and trapping of N-protected aziridines. N-tert-butylsulfonyl- (1) and N-tert-butylsulfinyl-protected aziridines (2) can be cleanly deprotonated and do not undergo ring opening or sulfenic acid elimination as described for related systems. 2 can also be used for diastereospecific α-lithiation leading to optically pure α-substituted aziridines.