While methyl- and benzylamines openedN-tosyl aziridines 1
very effciently in acetonitrile with complete regio- and stereoselectivity to give the corresponding diamines 2 and 3, respectively, in excellent yields, similar openings with water could only be achieved in the presence of a catalytic amount of cerium(IV)ammonium nitrate under very mild conditions furnishing the amino alcohols.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
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Did you bother to read how they prepared the aziridines?
The starting aziridines 1a–f were prepared from the corresponding epoxides in four steps: (a) ring opening of the epoxides with NaN3 in MeOH:H2O (8:1) in presence of NH4Cl22 (b) reduction of the resulting azides to amines using Ph3P in dry THF; (c) protection of the amines as tosylates using TsCl, Et3N in CH2Cl2 and (d) treatment of N-tosyl amino alcohols with diethyl azodicarboxylate and Ph3P in dry THF.
After step (b) the amino alcohol is already synthesized. Thus your suggested procedure is a method for turning amino alcohols into tosyl-aziridines and then back into amino alcohols, but this time with an N-tosyl group attached to it. Futile, I'd say.
I know they do it like that and turn back in the synthetic scheme only to prove that CAN catalyzed aziridine - aminoalcohol conversion is possible. But there are many ways of creating an aziridine. Then the method will be useful to open the ring. Not futile i think.
Here's an example of a aziridine synth. method
A Convenient Method for the Synthesis of 2-Arylaziridines from Styrene Derivatives via 2-Arylethenyl(diphenyl)sulfonium Salts
Styrene derivatives reacted with diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1) at low temperature to afford 2-arylethenyl(diphenyl)sulfonium triflates (2). Treatment of 2 with primary amines gave the corresponding 2-arylaziridines in high yields. One-pot synthesis of various aziridines was also successfully carried out without isolation of the intermediate 2
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
References
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c) For a review, see: A. J. Mancuso and D. Swern, Synthesis, 1981, 165.
8) Note without reference.
9) See: P. E. Fanta, in “Heterocyclic Compounds with Three- and Four-Membered Rings,” ed. by A. Weissberger, John Wiley and Sons, New York (1964), Part 1, p 527.
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