Non-terminal alkene ---Amino Ester via aziridine and without epoxide.

Aug 2013
I have noted several examples of non-terminal alkenes (I am considering 1-phenylcyclopentene (825-54-7) here) being directly oxidized to the appropriate n-substituted aziridine (in this case the N-methyl) using o-(2,4-Dinitrophenyl)-n-methylhydroxylamine (38100-39-9). Now, the trans amino-ester can be conveniently be made by ring-opened the aziridine & using the an ester synthesis using the appropriate acid chloride with triethylamine as solvent (removes loose HCl from reaction).

This route has shown up in several syntheses detailing the synthesis of N-methyl & unsubstituted aziridines and more frequently I have looked into the ring-opening of the aziridines. What is so convenient about it is that the products are almost 100% of the trans-pair which is VERY convenient.

If I have posted in the wrong place, forgive me. If it has been asked before, I apoligise.

I came across this class of route when researching a totally different area of chemistry but then I would occasionally bump into it or into a related compound. BOC & triflate groups are often added to those aziridines with an N-H bond from which I take the fact that unless that N-H is protected, side-reactions may be an issue.

If this is a name reaction and I'm just being dumb, post name and call me an idiot afterwards.

Many thanks.