Categories: C-N Bond Formation > Amines >
Synthesis of hydroxylamines
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Recent Literature
Bench stable N-Methyl-O-alkoxyformate hydroxylamine hydrochloride
reagents can be prepared in two high-yielding steps from N-Boc-N-methyl
hydroxylamine. Subsequent reaction with various carbonyl compounds give the
corresponding α-functionalised products in good yield via a proposed
[3,3]-sigmatropic rearrangement.
A. Hall, K. L. Jones, T. C. Jones, N. M. Killeen, R. Pörzig, P. H. Taylor, S. C.
Yau, N. C. O. Tomkinson, Synlett, 2006,
3435-3438.
Highly regioselective ring opening of epoxides with poor nucleophiles such as
indole, borane, O-trimethylsilylhydroxylamine, p-nitroaniline and
sterically hindered tert-butylamine is a fast and convenient reaction in
the presence of 5.0 M lithium perchlorate-Et2O solution (LPDE).
A. Heydari, M. Mehrdad, A. Maleki, N. Ahmadi, Synthesis, 2004,
1557-1558.
