ORGN 168 |
| Chiral N-Tfa and Fmoc-protected (α-aminoacyl)benzotriazoles undergo Friedel-Crafts-type reactions with indole, N-methylindole, pyrrole, N-methylpyrrole and benzene under mild conditions in the presence of AlCl3 with full preservation (>99%) of chirality as proven by HPLC. This efficient two-step sequence leads to the synthesis of a new class of enantiomerically pure α-amino ketones containing heterocyclic moieties which are potentially valuable biological and pharmacological compounds. (Scheme 1) Furthermore, N-Tfa and Fmoc-protected (α-aminoacyl)benzotriazoles with aromatic side chains, which can be obtained from α-amino acids such as phenylalanine and tryptophan, can undergo intramolecular acylation under the same conditions in absence of N-heterocycles. This intramolecular acylation provides a novel method to prepare polycyclic skeletons containing a chiral center. Scheme 1
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |
