ORGN 143 |
| The development of solid phase peptide synthesis has created a large demand for Fmoc-protected amino acids. Due the base lability of the Fmoc group, current syntheses of Fmoc-protected amino acids typically require multiple protecting group manipulations. Our goal is to explore more efficient syntheses of Fmoc-protected α- and β-amino acids using Fmoc-protected iminium ions as electrophiles. Toward this goal, we have prepared Fmoc-protected N,O-acetals as bench-stable reagents through simple condensation reactions. In the presence of Lewis acids, the N,O-acetals generate acyliminium ions, which react with weakly basic nucleophiles in a variety of C-C bond-forming reactions. We will describe applications of this chemistry to the syntheses of α- and β-amino acids. |
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Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster
Sci-Mix
Division of Organic Chemistry |