Categories: C-N Bond Formation, Synthesis of cyclic amines >
Synthesis of aziridines
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Recent Literature
The reaction of N-tosyl imines with in situ generated iodomethyllithium,
with a simple and rapid experimental protocol, allows an efficient and general
synthesis of aziridines. A reaction of a chiral aldimine derived from
phenylalaninal proceeded with high diastereoselectivity. A mechanism to explain
this novel reaction is proposed.
J. M. Concellón, H. Rodríguez-Solla, C. Simal, Org. Lett.,
2008,
10, 4457-4460.
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.
Montmorillonite K-10 as solid acid catalyzes a stereoselective reaction of
imines with ethyl diazoacetate to yield cis-aziridines. The reactions
proceeded readily at room temperature in short reaction times, providing the
products in very good yields and exclusive selectivity.
D. Borkin, A. Carlson, B. Török, Synlett, 2010,
745-748.
The tertiary amine DABCO catalyzes the reaction of imines with phenacyl bromide
derivatives to afford functionalized aziridines in high yields and
stereoselectivities in a one-pot process - including the formation of ylides and
their precursors.
L. D. S. Yadav, R. Kapoor, Garima, Synlett, 2009,
3123-3126.
A mild, convenient protocol for the synthesis of cis-aziridines
employs a catalytic amount of Brřnsted 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.
A clean and fast aziridination of diazoacetamides with N-Boc-imines, as
well as N-Cbz-imines, catalyzed by a chiral phosphoric acid in DCM at
room temperature achieves excellent yields, diastereoselectivities,
chemoselectivities, and enantioselectivities.
X. Zeng, X. Zeng, Z. Xu, M. Lu, G. Zhoung, Org. Lett., 2009,
11, 3036-3039.
