Categories: C-N Bond Formation, Synthesis of cyclic amines >
Synthesis of aziridines
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Name Reactions
Recent Literature
Aldimines (generated in situ from aldehydes and amines) react readily with
ethyl diazoacetate in the presence of 2 mol% of Bi(OTf)3 in
[bmim]PF6 to produce the corresponding aryl aziridine
carboxylates in high yields with excellent cis-diastereoselectivity.
J. S. Yaday, B. V. S. Reddy, P. N. Reddy, M. Shesha Rao, Synthesis,
2003, 1387-1389.
A mild, convenient protocol for the synthesis of cis-aziridines
employs a catalytic amount of Brønsted acid. Diazo compound decomposition
via alkylation or homocoupling upon exposure to a proton source is slow
relative to [2 + 1] annulation in the presence of a Schiff base.
A. L. Williams, J. N. Johnston, J. Am. Chem. Soc.,
2004,
126, 1612-1613.
