Hi Greg (and Markus, Peter, et al.),
Personal opinion - my vote would be to always keep the chiral information at
3-valent nitrogen centres...
As Peter pointed-out, there are bridgehead examples (most of which, I guess,
will have additional carbon chiral centres - and offer diastereomeric
considerations).
There are also, I believe, some nice oxaziridine examples where the oxaziridine
N is the only chiral centre present (interpreted from abstract here:
http://dx.doi.org/10.1039/C39850000998):
3,3-dimethyl (2S)-2-tert-butyloxaziridine-3,3-dicarboxylate
COC(=O)C1(O[N@]1C(C)(C)C)C(=O)OC
and many other examples of diastereomeric oxaziridines - where the N is a
chiral centre - eg see http://dx.doi.org/10.1016/j.tetasy.2008.09.016
Kind regards
James
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