O-Alkylation of hydroxylamines, oximes and related compounds

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A direct preparation of O-substituted hydroxylamines from alcohols is described by O-alkylation of tert-butyl N-hydroxycarbamate with the methanesulfonates of respective alcohols, followed by acidic N-deprotection.
S. Albrecht, A. Defoin, C. Tarnus, Synthesis, 2006, 1635-1638.

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.

An organocatalytic β-hydroxylation of α,β-unsaturated aldehydes with commercially available (E)-benzaldehyde oxime gives the corresponding chiral carbonyl β-oxime ethers in high yields and with excellent enantioselectivities. The chiral carbonyl β-oxime ethers can be reduced to the corresponding 1,3-diols in high yields.
S. Bertelsen, P. Dinér, R. L. Johansen, K. A. Jørgensen, J. Am. Chem. Soc., 2007, 129, 1536-1537.

The oxygen atom of hydroxylamines having an N-electron-withdrawing substituent (also known as hydroxamic acids) acts as a reactive nucleophile in transition-metal-catalyzed allylic substitutions. The palladium-catalyzed O-allylic substitution of hydroxylamines with allylic carbonate afforded linear hydroxylamines, whereas branched hydroxylamines were observed in iridium-catalyzed reactions.
H. Miyabe, K. Yoshida, M. Yamauchi, Y. Takemoto, J. Org. Chem., 2005, 70, 2148-2153.

H. Miyabe, K. Yoshida, M. Yamauchi, Y. Takemoto, J. Org. Chem., 2005, 70, 2148-2153.

A new reaction condition for Michael addition of oximes onto activated olefins has been discovered using a catalytic amount of triphenylphosphine. Various aldoximes and ketoximes were reacted with different Michael acceptors in good yields.
D. Bhuniya, S. Mohan, S. Narayanan, Synthesis, 2003, 1018-1024.

D. Bhuniya, S. Mohan, S. Narayanan, Synthesis, 2003, 1018-1024.