Mild and efficient deprotection of the amine protecting p-methoxyphenyl (PMP) group

Efficient and scalable oxidative cleavage procedures for the amine protecting p-methoxyphenyl (PMP) group are described. Mild and efficient procedures for deprotection of the amine nitrogen protecting p-methoxyphenyl (PMP) group are described. Periodic acid and trichloroisocyanuric acid (TCCA) were...

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Bibliographic Details
Published in:Tetrahedron letters 2006-11, Vol.47 (46), p.8109-8113
Main Authors: Verkade, Jorge M.M., van Hemert, Lieke J.C., Quaedflieg, Peter J.L.M., Alsters, Paul L., van Delft, Floris L., Rutjes, Floris P.J.T.
Format: Article
Language:English
Subjects:
Asymmetric Mannich reactions
Organocatalysis
Oxidative deprotection
p-Methoxyphenyl (PMP) deprotection
β-Amino acids
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Summary:Efficient and scalable oxidative cleavage procedures for the amine protecting p-methoxyphenyl (PMP) group are described. Mild and efficient procedures for deprotection of the amine nitrogen protecting p-methoxyphenyl (PMP) group are described. Periodic acid and trichloroisocyanuric acid (TCCA) were found to be particularly effective in realizing amine liberation using 1 and 0.5 equiv of the oxidant, respectively. Extension of the periodic acid-mediated conditions to simultaneous alcohol oxidation by combination with a catalytic amount of sodium dichromate led to smooth conversion of PMP-protected Mannich products into the corresponding β-amino acids in a one-pot procedure.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.09.044