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.
The reaction of trimethylsilyldiazomethane with N-sulfonyl (Ts and SES)
imines provides aziridines in good yields and high cis
stereoselectivities. The silyl group can be substituted by treatment with a
fluoride source and electrophiles again with high selectivity. In addition,
complete regioselectivity is observed in ring opening reactions of these
aziridines with nucleophiles.
V. K. Aggarwal, M. Ferrara,
Org. Lett., 2000, 2, 4107-4110.
A visible light-promoted divergent cycloaddition of α-diazo esters to
hexahydro-1,3,5-triazines provides a series of aziridines and imidazolidines in
good yield, by simply changing the reaction media. The reactions occur under
visible light irradiation without photoredox catalysts.
X. Cheng, B.-G. Cai, H. Mao, J. Lu, L. Li, K. Wang, J. Xuan, Org. Lett., 2021, 23,
4109-4114.
Adducts derived from P(NMe2)3 and α-ketoesters are
effectively intercepted by N-sulfonyl imines, affording a range of
aziridine-2-carboxylates. The diastereoselectivity of this aziridination depends
on steric hindrance from substituents on the substrates.
J. Jiang, H. Liu, C.-D. Lu, Y.-J. Xu, J. Org. Chem.,
2017, 82, 811-818.
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.