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For recent examples, see: (a) Hodgson, D. M.; Stent, M. A. H.; Stefane, B.; Wilson, F. X. Org. Biomol. Chem. 2003, 1, 1139; (b) Hodgson, D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Stent, M. A. H.; Matthews, I. R.; Wilson, F. X.; Witherington, J. Angew. Chem., Int. Ed. 2002, 41, 4313; (c) Hodgson, D. M.; Gras, E. Angew. Chem., Int. Ed. 2002, 41, 2376; (d) Hodgson, D. M.; Cameron, I. D.; Christlieb, M.; Green, R.; Lee, G. P.; Robinson, L. A. J. Chem. Soc., Perkin Trans. 1 2001, 2161; (e) Hodgson, D. M.; Robinson, L. A.; Jones, M. L. Tetrahedron Lett. 1999, 40, 8637; (f) Hodgson, D. M.; Maxwell, C. R.; Matthews, I. R. Tetrahedron: Asymmetry 1999, 10, 1847.
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For recent examples, see: (a) Hodgson, D. M.; Stent, M. A. H.; Stefane, B.; Wilson, F. X. Org. Biomol. Chem. 2003, 1, 1139; (b) Hodgson, D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Stent, M. A. H.; Matthews, I. R.; Wilson, F. X.; Witherington, J. Angew. Chem., Int. Ed. 2002, 41, 4313; (c) Hodgson, D. M.; Gras, E. Angew. Chem., Int. Ed. 2002, 41, 2376; (d) Hodgson, D. M.; Cameron, I. D.; Christlieb, M.; Green, R.; Lee, G. P.; Robinson, L. A. J. Chem. Soc., Perkin Trans. 1 2001, 2161; (e) Hodgson, D. M.; Robinson, L. A.; Jones, M. L. Tetrahedron Lett. 1999, 40, 8637; (f) Hodgson, D. M.; Maxwell, C. R.; Matthews, I. R. Tetrahedron: Asymmetry 1999, 10, 1847.
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85031131728
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In Müller's original report (see Ref. 9), the sense of induction in the rearrangement of a norbornene-derived N-tosyl aziridine was established by chemical correlation but the low magnitude of the optical rotation cast potential doubt over this result. However, Müller has now confirmed that this and two new examples are indeed consistent with lithiation of the S-aziridine stereocentre, as we have observed: Müller, P.; Riegert, D.; Bernardinelli, G. personal communication.
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In Müller's original report (see Ref. 9), the sense of induction in the rearrangement of a norbornene-derived N-tosyl aziridine was established by chemical correlation but the low magnitude of the optical rotation cast potential doubt over this result. However, Müller has now confirmed that this and two new examples are indeed consistent with lithiation of the S-aziridine stereocentre, as we have observed: Müller, P.; Riegert, D.; Bernardinelli, G. personal communication.
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