Categories: C-O Bond Formation >
O-Alkylation of hydroxylamines, oximes and related compounds
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Recent Literature
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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.

The rate of the proline-catalyzed α-aminoxylation of aldehydes is significantly
increased in the presence of a bifunctional urea originating from the hydrogen
bonding interaction between the bifunctional urea and an oxazolidinone
intermediate to increase the rate of enamine formation.
S. L. Poe, A. R. Bogdan, B. P. Mason, J. L. Steinbacher, S. M. Opalka, D. T.
McQuade, J. Org. Chem., 2009,
74, 1574-1580.

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.

