Categories: C-N Bond Formation, Synthesis of cyclic amines >
Synthesis of aziridines
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Recent Literature
A mild, efficient, and selective aziridination of olefins with p-toluenesulfonamide catalyzed by
dirhodium(II) caprolactamate is described. Aziridine formation occurs
through aminobromination and subsequent base-induced ring
closure.
A. J. Catino, J. M. Nichols, R. E. Forslund, M. P. Doyle, Org. Lett., 2005,
7, 2787-2790.
N-N ylides for the aziridination of a range of enone systems can be prepared by
in situ amination of a tertiary amine. The amine may be used
sub-stoichiometrically, and promising levels of enantioselectivity are observed
with quinine as promoter.
A. Armstrong, C. A. Baxter, S. G. Lamont, A. R. Pape, R. Wincewicz, Org. Lett., 2007,
9, 351-353.
An efficient and practical aminohalogenation and in situ intramolecular SN2
substitution of α,β-unsaturated esters and ketones gave N-p-tosyl-aziridine-2-ketones
and carboxylates in moderate to good yields and excellent anti
stereoselectivity. Triethylamine was found to be an effective base for the in
situ cyclization for most substrates.
D. Chen, C. Timmons, L. Guo, X. Xu, G. Li, Synthesis,
2004, 2479-2484.
D. Chen, C. Timmons, L. Guo, X. Xu, G. Li, Synthesis,
2004, 2479-2484.
A gold(I) compound, supported by 4,4',4' '-tri-tert-butyl-2,2':6',2' '-terpyridine
(tBu3tpy) as the ligand, efficiently catalyzes olefin
aziridination with the use of the commercially available oxidant PhI(OAc)2
and sulfonamides.
Z. Li, X. Ding, C. He, J. Org. Chem., 2006,
71, 5876-5880.
An electrochemical aziridination process is described that delivers a
nitrene functionality to olefins from N-aminophthalimide. Remarkably,
both electron-rich and electron-poor olefins are converted to aziridines
with high efficiency. The selectivity is discussed.
T. Siu, A. K. Yudin, J. Am. Chem. Soc., 2002,
124,
530-531.
A straightforward synthesis of aziridines is reported from electron-rich
azides, electron-deficient olefins, and triflic acid in cold
acetonitrile. Ester substrates bearing a nucleophilic carbonyl give products of
an olefin
aminohydroxylation.
J. M. Mahoney, C. R. Smith, J. N. Johnston, J. Am. Chem. Soc.,
2005,
127, 1354-1355.
