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