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Synfacts 2008(10): 1120-1120
DOI: 10.1055/s-2008-1078192
DOI: 10.1055/s-2008-1078192
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Solid-Phase Conversion of Aromatic Acetylenes to Carbonyl Compounds
S. T. Le Quement, T. E. Nielsen, M. Meldal*
Carlsberg Laboratory, Valby, Denmark
Further Information
Publication History
Publication Date:
22 September 2008 (online)
Significance
Solid-phase conversion of aromatic acetylenes 1 to the corresponding carboxylic acids 2, α-ketocarboxylic acids 3, and methyl ketones 4 is described. Resin-bound TMS-acetylenes 1 were prepared from PEGA resin by Fmoc-based peptide synthesis. The desilylation of 1 with TBAF (4 equiv) followed by OsO4/NMO/HMTA-mediated oxidative cleavage to give the carboxylic acids 2. α-Ketocarboxylic acids 3 were obtained by direct treatment of 1 with OsO4/NMO/HMTA and ketones 4 by acid-mediated hydration of 1 using aqueous TFA.