Author/Authors :
Verkade، نويسنده , , Jorge M.M. and van Hemert، نويسنده , , Lieke J.C. and Quaedflieg، نويسنده , , Peter J.L.M. and Alsters، نويسنده , , Paul L. and van Delft، نويسنده , , Floris L. and Rutjes، نويسنده , , Floris P.J.T.، نويسنده ,
Abstract :
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.
Keywords :
p-Methoxyphenyl (PMP) deprotection , ?-Amino acids , Asymmetric Mannich reactions , organocatalysis , Oxidative deprotection
