Journal
TETRAHEDRON LETTERS
Volume 47, Issue 46, Pages 8109-8113Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2006.09.044
Keywords
p-methoxyphenyl (PMP) deprotection; beta-amino acids; asymmetric Mannich reactions; organocatalysis; oxidative deprotection
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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 beta-amino acids in a one-pot procedure. (c) 2006 Elsevier Ltd. All rights reserved.
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