ORGN 193 |
Fmoc (9-fluorenylmethoxycarbonyl) is a useful protective group amino acids and Fmoc-protected amino acids are widely utilized as a building block for peptides synthesis. Usually, the Deprotection of Fmoc can be achieved under basic conditions in the presence of piperidine or morpholine as a base. Therefore, Fmoc protective group could not be applicable to the substrates containing base labile functional groups. During the course of our study to develop the hydrogenation using heterogeneous Pd/C catalyst, we found that the Fmoc protective group was cleaved under the neutral Pd/C catalyzed hydrogenation conditions at room temperature. Interestingly, the addition of MeCN into the reaction mixture dramatically accelerated the reaction rate. The present reductive method is applicable as a mild and general Fmoc deprotection method. |
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |