N-tosyl-(S)-2-methylaziridine from (2S,3R)-threonine?
After numerous edits, I think I've answered my own question. Correct me if I'm rong...
The usual technique for preparing aziridines from amino acids is:
Reduction to the amino alcohol
N- and O-Tosylation followed by cyclization
The aziridine formed has the same orientation as the -NH2.
The decarboxylation product of L-threonine is 2R-(-)-2-Hydroxypropylamine, which should also yield an aziridine using the same procedure.
Assuming the aziridine is formed by SN2, the configuration will be inverted with respect to the -OH, resulting in the (S) enantiomer.
Now to find a straightforward (and inexpensive) way of inverting secondary alcohols...
Thanks for watching =)
[Edited on 12-4-2011 by dean stark]
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