The synthesis of β-N-tosylamino hydroxylamines via the ring opening of N-tosylaziridines and their use in reverse Cope cyclisations

N-Tosylated aziridines have been found to undergo high yielding and regioselective ring opening with hydroxylamines in diethyl ether in the presence of boron trifluoride diethyl ether complex to give β-N-tosylamino hydroxylamines. Suitable substrates were shown to undergo reverse-Cope cyclisations to give amino functionalised pyrrolidine and piperidine N-oxides.