ORGN 472 |
| Amino acid conjugated with steroid, sugar, terpenes and long chain alcohols are important in various biological processes. Many previous esterification methodologies have tried to mimic these reactions. However, these literature methodologies are not ideal because an efficient esterification procedure would incorporate (i) simple preparative procedures, (ii) mild reaction conditions whereby not affecting other functionalities, (iii) preservation of the original chirality. The conventional methods above do not meet these requirements and hence there is a need for further improved O-aminoacylation procedures. Herein, we present microwave assisted novel methodology for the preparation of chiral N-(protected- &alpha-aminoacyl)esters from readily available N-(Z-&alpha-aminoacyl)benzotriazoles and naturally occurring terpenes, steroids, long chain aliphatic alcohols, and protected sugars. Compounds were obtained in average isolated yield of 65—96% with complete retention of the original chirality as observed in NMR and HPLC analysis. This work has been carried out under the guidance of Prof. Alan. R. Katritzky.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |